Tetrahydrofuran → HCID 86586577, compound

HRID 895850Notes

Reaction equation

HRID 895850 reaction equation
O.[F-].[CH2:3]([N+](CCCC)(CCCC)CCCC)[CH2:4][CH2:5]C.[CH3:20][C:21]1([CH3:55])[C@@H:51]([OH:52])[CH2:50][CH2:49][C@@:48]2([CH3:53])[C:22]1=[CH:23][CH:24]=[C:25]1[C@@H:47]2[CH2:46][CH2:45][C@@:44]2([CH3:54])[C@H:26]1[CH2:27][CH2:28][C@@H:29]2[C@@H:30]([CH2:32][O:33][Si](C(C)C)(C(C)C)C(C)C)[CH3:31].[O:56]1[CH2:60][CH2:59][CH2:58][CH2:57]1>>[C:60]([OH:56])(=[O:33])[C:59]1[CH:5]=[CH:4][CH:3]=[CH:57][CH:58]=1.[CH3:55][C:21]1([CH3:20])[C@@H:51]([OH:52])[CH2:50][CH2:49][C@@:48]2([CH3:53])[C:22]1=[CH:23][CH:24]=[C:25]1[C@@H:47]2[CH2:46][CH2:45][C@@:44]2([CH3:54])[C@H:26]1[CH2:27][CH2:28][C@@H:29]2[C@H:30]([CH3:31])[CH2:32][OH:33]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 162116731-Butanaminium, N,N,N-tributyl-, fluoride, hydrateHCID 69790268HCID 69790268, compound

Product 1

HCID 86586577HCID 86586577, compound

Procedure

2 g pulverized molecular sieve (4 Å) and 1.27 g tetrabutylammoniumfluoride hydrate were added to a solution of 2.0 g (20S)-4,4-dimethyl-20-[((triisopropylsilyl)oxy)methyl]-pregna-5,7-dien-3β-ol in 50 ml tetrahydrofuran were added. The mixture was stirred overnight at room temperature, concentrated under reduced pressure and purified by column chromatography to give 1.17 g of (20S)-4,4,20-trimethyl-pregna-5,7-dien-3β,21-diol benzoate.

Workup

  1. additionwere added
  2. concentrationconcentrated under reduced pressure
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-93dae63d72b8459aa56333b9abebe768
Source dataset
uspto-grants-2005_07
Patent number
US06916921B2

Reaction notes

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