Below is the H-NMR correlation of the starting material of the Birch and Bouveault-Blanc Reduction, methyl enol ether 12.
Peak ppm value (integration, splitting) | Correlation | Explanation |
7.31 (s, 1H) | D | Only single hydrogen that is entirely isolated and deshielded. |
6.53 (d, J = 10.2 Hz 1H) | B/C | Within aromatic range with one three bond neighbor. |
6.40 (d, J = 8.1 Hz, 1H) | B/C | Within aromatic range with one three bond neighbor. |
6.35 (d, J = 9.9 Hz, 1H) | I | Does not have an HSQC correlation because it is on an amide, is higher because it is attached to a Boc group. |
5.34 (ddd, J = 13.3, 10.3, 3.5 Hz, 1H) |
G | Split by I, E, and F (E and F are diastereotopic). |
4.95 (d, J = 3.0 Hz, 1H) | O | Hydrogen on an sp2 carbon double bond that is split by a single hydrogen neighbor T. |
4.61-4.49 (m, 2H) | M, N | Correlates to a 2H peak on the HMBC, is mixed in with the multiplet. |
4.50 (q, J = 4.0 Hz, 1H) | P | Is mixed in to the multiplet range and is split by two hydrogens. It is inferred that a quartet was mistaken for a doublet of doublets as P and Q are diastereotopic. |
4.15 (d, J = 8.0 Hz, 1H) | J | Has one three bond neighbor and inferred by HMBC from the assignment of L. |
3.66 (d, J = 13.3 Hz, 1H) | Q | Is split by the broad singlet R. It is inferred that the diastereotopicity of Q and P wasn't enough to create a predicted doublet of doublets at this ppm. |
3.44 (s, 3H) | K | Three hydrogen peak, only methoxy group that is part of an ester so it would be highest. |
3.39 (bs, 1H) | R | Is on a double bond in an allyl group. |
3.28 (s, 3H) | S | HMBC indicates that the 3 hydrogen group correlates with this signal. |
3.14 (s, 3H) | A | HMBC data indicates that it is not as correlated with hydrogen T. |
2.49 (dt, J = 13.5, 4.3 Hz, 1H) | L | HMBC data correlates it to the carbonyl and methoxy group K. |
2.41 (d, J = 15.1 Hz, 1H) | E/F | Diastereotopic, is correlated with the HMBC and hydrogen G. |
2.26 (dd, J = 13.8, 5.7 Hz, 1H) |
E/F | Diastereotopic, is correlated with the HMBC and hydrogen G. |
1.84 (t, J = 13.0 Hz, 1H) | T | Neighbor to aromatic carbon and has two three-bond neighbors. |
1.41 (s, 9H) | H | Boc group structure with 9H's. |