Ethanol → HCID 10938669, compound

HRID 1197195Notes

Reaction equation

[Li].[O:2]1[C@H:4]2[C:5](=[O:31])[CH:6]=[C:7]3[C@:28]([CH3:29])([C@@H:3]12)[C@@H:27]1[C@H:10]([C@H:11]2[C@:24]([CH3:30])([CH2:25][CH2:26]1)[C@@H:14]([C@H:15]([CH3:23])[CH2:16][CH2:17][C:18](=[O:22])[CH:19]([CH3:21])[CH3:20])[CH2:13][CH2:12]2)[CH:9]=[CH:8]3.C(O)C>[NH4+].O1CCCC1>[OH:2][C@@H:3]1[C@@:28]2([CH3:29])[C:7](=[CH:8][CH2:9][C@@H:10]3[C@@H:27]2[CH2:26][CH2:25][C@@:24]2([CH3:30])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C@H:15]([CH3:23])[CH2:16][CH2:17][CH:18]([OH:22])[CH:19]([CH3:21])[CH3:20])[CH2:6][C@@H:5]([OH:31])[CH2:4]1

Participants

Conditions

Temperature: -75 °C

Procedure

First, 1.80 g (35 equivalent amount) of metal lithium was dissolved in 130 ml of liquid ammonium under a nitrogen atmosphere and to the solution 3.00 g of 1α, 2α-epoxycholesta-4,6-dien-3,24- dione dissolved in 150 ml of tetrahydrofuran was dropwise added for 90 minutes while maintaining the temperature of the reaction mixture at -75° C. Then 60 minutes later, the temperature of the reaction mixture was increased to -34° C. for about 30 minutes and to the mixture was dropwise added 40.3 g (120 equivalent amount) of ethanol. Stirring was continued until the lithium layer floating as a liquid layer on the reaction mixture disappeared. Next, after evaporating most of the ammonia from the reaction mixture at room temperature, the same procedure as described in Reference Example 1 was carried out to obtain 1α, 3β, 24-trihydroxycholest-5-ene at a yield of 63%.

Workup

additionwas dropwise added for 90 minutes
temperatureThen 60 minutes later, the temperature of the reaction mixture was increased to -34° C. for about 30 minutes and to the mixture
customNext, after evaporating most of the ammonia from the reaction mixture at room temperature

Sources & evidence

ORD record: ord-54e1fb4be5b3489a947e1d7448a73abf
Source dataset: uspto-grants-1992_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05117015

Reaction notes

Loading…