Acetic Anhydride → HCID 69306254, compound

HRID 895839Notes

Reaction equation

HRID 895839 reaction equation
[CH3:1][C:2]1([CH3:36])[C@@H:32]([OH:33])[CH2:31][CH2:30][C@@:29]2([CH3:34])[C:3]1=[CH:4][CH2:5][C@@H:6]1[C@@H:28]2[CH2:27][CH2:26][C@@:25]2([CH3:35])[C@H:7]1[CH2:8][CH2:9][C@@H:10]2[C@@H:11]([CH2:13][O:14][Si:15]([CH:22]([CH3:24])[CH3:23])([CH:19]([CH3:21])[CH3:20])[CH:16]([CH3:18])[CH3:17])[CH3:12].[C:37]([O:40]C(=O)C)(=[O:39])[CH3:38]>N1C=CC=CC=1>[C:37]([OH:40])(=[O:39])[CH3:38].[CH3:36][C:2]1([CH3:1])[C:32](=[O:33])[CH2:31][CH2:30][C@@:29]2([CH3:34])[C:3]1=[CH:4][CH2:5][C@@H:6]1[C@@H:28]2[CH2:27][CH2:26][C@@:25]2([CH3:35])[C@H:7]1[CH2:8][CH2:9][C@@H:10]2[C@@H:11]([CH2:13][O:14][Si:15]([CH:19]([CH3:21])[CH3:20])([CH:16]([CH3:18])[CH3:17])[CH:22]([CH3:23])[CH3:24])[CH3:12]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 11386782HCID 11386782, compound

Product 1

HCID 69306254HCID 69306254, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 18.2 g (20S)-4,4-dimethyl-20-[((triisopropylsilyl)oxy)methyl]-pregna-5-en-3β-ol in 175 ml pyridine 6.24 ml of acetic anhydride were added at room temperature. The reaction mixture was stirred for 20 hours and then poured into an ice/hydrochloric acid mixture. This was extracted with ethyl acetate. The organic layers were combined, washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to give 16.2 g (20S)-4,4-dimethyl-20-[((triisopropylsilyl)oxy)methyl]-pregna-5-en-3-one acetate as a white solid, which was used without further purification.

Workup

  1. extractionThis was extracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dc41793c06cc40aabe95267d2cb65f98
Source dataset
uspto-grants-2005_07
Patent number
US06916921B2

Reaction notes

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