Pivaloyl chloride → HCID 66859795, compound

HRID 1661129Notes

Reaction equation

HRID 1661129 reaction equation
[C:1](Cl)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[CH2:8]([O:15][C:16]1[CH:33]=[CH:32][C:31]2[C@@H:30]3[C@H:21]([C@H:22]4[C@@:26]([CH2:28][CH2:29]3)([CH3:27])[C:25]([C:35]([F:38])([F:37])[F:36])([OH:34])[CH2:24][CH:23]4[CH2:39][CH2:40][CH2:41][CH2:42][OH:43])[CH2:20][CH2:19][C:18]=2[CH:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>N1C=CC=CC=1>[CH2:8]([O:15][C:16]1[CH:33]=[CH:32][C:31]2[C@@H:30]3[C@H:21]([C@H:22]4[C@@:26]([CH2:28][CH2:29]3)([CH3:27])[C:25]([OH:34])([C:35]([F:38])([F:36])[F:37])[CH2:24][CH:23]4[CH2:39][CH2:40][CH2:41][CH2:42][O:43][C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3])[CH2:20][CH2:19][C:18]=2[CH:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 66860433HCID 66860433, compound

Product 1

HCID 66859795HCID 66859795, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Pivaloylchloride (0.50 ml; 4.10 mmol) was added dropwise to a solution of 3-Benzyloxy-15-(4-hydroxybutyl)-17-trifluoromethyl-estra-1,3,5(10)-trien-17-ol (1.65 g; 3.28 mmol) in pyridine (15 ml) at 0° C. After stirring for 2 h, the reaction mixture was poured into ice water and stirred for another h. After extraction with DCM, the combined organic phases were dried over MgSO4. After evaporation of the solvent, the residue was purified by column chromatography (SiO2, DCM) yielding the title compound (1.85 g, 96%) as colourless oil.

Workup

  1. stirringstirred for another h
  2. extractionAfter extraction with DCM
  3. dry with materialthe combined organic phases were dried over MgSO4
  4. customAfter evaporation of the solvent
  5. customthe residue was purified by column chromatography (SiO2, DCM)

Sources & evidence

ORD record
ord-9e95ef4e3f0140419b474213617045c4
Source dataset
uspto-grants-2011_10
Patent number
US08030298B2

Reaction notes

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