Pivaloyl chloride → HCID 66859795, compound

HRID 2088525Notes

Reaction equation

HRID 2088525 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 colorless 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-2ac5547898034745bb40a2a8c0410e1e
Source dataset
uspto-grants-2013_05
Patent number
US08435973B2

Reaction notes

Loading…