Bis[alpha,alpha-bis(trifluoromethyl)benzenemethanolato]diphenylsulfur → 3beta-Benzoyloxy-14alpha-cyano-4,4-dimethyl-5alpha-cholest-6-ene

HRID 1493667Notes

Reaction equation

HRID 1493667 reaction equation
[C:1]([O:9][C@H:10]1[CH2:34][CH2:33][C@@:32]2([CH3:35])[C@@H:12]([CH2:13][CH:14](O)[C@@H:15]3[C@@H:31]2[CH2:30][CH2:29][C@@:28]2([CH3:36])[C@@:16]3([C:37]#[N:38])[CH2:17][CH2:18][C@@H:19]2[C@H:20]([CH3:27])[CH2:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[C:11]1([CH3:41])[CH3:40])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC(C(OS(OC(C(F)(F)F)(C(F)(F)F)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C(F)(F)F)C(F)(F)F)=CC=1>ClCCl>[C:1]([O:9][C@H:10]1[CH2:34][CH2:33][C@@:32]2([CH3:35])[C@@H:12]([CH:13]=[CH:14][C@@H:15]3[C@@H:31]2[CH2:30][CH2:29][C@@:28]2([CH3:36])[C@@:16]3([C:37]#[N:38])[CH2:17][CH2:18][C@@H:19]2[C@H:20]([CH3:27])[CH2:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[C:11]1([CH3:41])[CH3:40])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 3608068Bis[alpha,alpha-bis(trifluoromethyl)benzenemethanolato]diphenylsulfur2×HCID 679240793beta-Benzoyloxy-14alpha-cyano-4,4-dimethyl-5alpha-cholestan-7-ol

Product 1

HCID 679249383beta-Benzoyloxy-14alpha-cyano-4,4-dimethyl-5alpha-cholest-6-eneYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3β-benzoyloxy-14α-cyano-4,4-di-methyl-5α-cholestan-7-ol (100 mg, 0.18 mmole) prepared as in Example 13(iv), in dichloromethane (2.5 mL) held at -78° C. was added Martin sulfurane dehydrating agent (bis [α,α-bis(trifluoromethyl)benzenemethanolato]-diphenyl-sulfur) (240 mg, 0.36 mmole) in dichloromethane (2.5 mL). The mixture was warmed to ambient temperature, stirred for an additional 6 hours, concentrated in vacuo and the residue was triturated with methanol to give 3β-benzoyloxy-14α-cyano-4,4-dimethyl-5α-cholest-6-ene (80 mg, 82%); mp 232°-233° C. (from CH2Cl2/MeOH).

Workup

  1. customheld at -78° C.
  2. concentrationconcentrated in vacuo
  3. customthe residue was triturated with methanol

Sources & evidence

ORD record
ord-45d113679a8f48098c75c7738cd22589
Source dataset
uspto-grants-1991_06
Patent number
US05023250

Reaction notes

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