HCID 53802218, compound → HCID 54193868, compound

HRID 1639181Notes

Reaction equation

HRID 1639181 reaction equation
CC(C)(C)C([O:5][C@@H:6]1[CH2:23][C@@:21]2([CH3:22])[C@@H:17]([CH2:18][CH2:19][C@@H:20]2[O:24]C(=O)C(C)(C)C)[C@H:16]2[C@H:7]1[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=1[C:14](=[O:31])[CH2:15]2)=O>CO>[OH:5][C@@H:6]1[CH2:23][C@@:21]2([CH3:22])[C@@H:17]([CH2:18][CH2:19][C@@H:20]2[OH:24])[C@H:16]2[C@H:7]1[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=1[C:14](=[O:31])[CH2:15]2

Participants

3

Reactant 1

HCID 53802218HCID 53802218, compound

Product 1

HCID 54193868HCID 54193868, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Hydrolysis of the keto diester (16A) (158 mg) in the above manner gave the keto diol (5A) (74 mg, 74%), m.p. 205°-208° C. (from methanol, νmax 3600 (OH) and 1680 cm-1 (C=O), δ (250 MHz) 8.13 (1 H, dd, J 8 and 0.5 Hz, aromatic proton), 8.04 (1 H, dd, J 7 and 1,5 Hz, aromatic proton), 7.56 (1 H, dt, J 8 and 1.5 Hz, aromatic proton), 7.36 (1 H, dt, J 7 and 0.5 Hz, aromatic proton), 4.32 (1 H, ddd, J 10.5, 9.5, and 5 Hz, 11-proton), 3.79 (1 H, t, J 8 Hz, 17-proton), 2.77 (1 H, dd, J 17 and 3.5 Hz, 7-proton), 2.5 (1 H, t, J 10.5 Hz, 9-proton), 2.41-1.22 (11 H, m), 0.79 (3 H, s, 18-CH3), (Found: M 286.1572. C18H22O3 requires M 286.1567).

Sources & evidence

ORD record
ord-b9c7ef8ad97846658490c95b0ebbccf0
Source dataset
uspto-grants-1989_11
Patent number
US04882439

Reaction notes

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