Benzoyl chloride → HCID 69284610, compound

HRID 566885Notes

Reaction equation

[CH3:1][C:2]([Si:5]([CH3:33])([CH3:32])[O:6][CH2:7][C@@H:8]([CH3:31])[C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[C:16]([C:17]([CH3:30])([CH3:29])[C@@H:18]([OH:28])[CH2:19][CH2:20]2)=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)([CH3:4])[CH3:3].[C:34](Cl)(=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>N1C=CC=CC=1>[C:34]([O:28][C@H:18]1[CH2:19][CH2:20][C@@:21]2([CH3:22])[C:16](=[CH:15][CH2:14][C@@H:13]3[C@@H:23]2[CH2:24][CH2:25][C@@:26]2([CH3:27])[C@H:12]3[CH2:11][CH2:10][C@@H:9]2[C@H:8]([CH3:31])[CH2:7][O:6][Si:5]([C:2]([CH3:3])([CH3:1])[CH3:4])([CH3:32])[CH3:33])[C:17]1([CH3:30])[CH3:29])(=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

Conditions

Temperature: 0 °C

Procedure

v)—A solution of the alcohol 6 (132.5 g) obtained in the previous step in dry pyridine (1310 ml) was cooled to 0° C. Benzoyl chloride (65.7 ml) was added in 5 min. and the reaction mixture was stirred for 1 h at room temperature. Then it was poured into ice-water (6650 ml) and the resulting suspension was stirred over-night. The precipitate was collected by filtration and washed with water (40-50° C.). The residue was dried and purified by crystallization from acetone to give (3β,20S)-21-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4,4,20-trimethylpregn-5-en-3-ol benzoate (7) (113.6 g).

Workup

stirringthe resulting suspension was stirred over-night
filtrationThe precipitate was collected by filtration
washwashed with water (40-50° C.)
customThe residue was dried
custompurified by crystallization from acetone

Sources & evidence

ORD record: ord-6002752a86274886b0e05e7deecb77c9
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06177420B1

Reaction notes

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