Methanol → HCID 14299659, compound

HRID 1576351Notes

Reaction equation

HRID 1576351 reaction equation
[C:1]([O:4][C:5]1[CH:22]=[CH:21][C:20]2[C@@H:19]3[C@H:10]([C@H:11]4[C@@:15]([CH2:17][CH2:18]3)([CH3:16])[C@@H:14]([OH:23])[CH2:13][CH2:12]4)[CH2:9][CH2:8][C:7]=2[CH:6]=1)(=[O:3])[CH3:2].[C:24](Cl)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CO>N1C=CC=CC=1.O>[C:1]([O:4][C:5]1[CH:22]=[CH:21][C:20]2[C@@H:19]3[C@H:10]([C@H:11]4[C@@:15]([CH2:17][CH2:18]3)([CH3:16])[C@@H:14]([O:23][C:24](=[O:31])[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:13][CH2:12]4)[CH2:9][CH2:8][C:7]=2[CH:6]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 887MethanolHCID 7412Benzoyl chlorideHCID 9818306Estradiol acetate

Product 1

HCID 14299659HCID 14299659, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

3-Acetoxy-oestra-1,3,5(10)-trien-17β-ol (500 mg., 1.6 mmole) in pyridine (2 ml.) was treated with benzoyl chloride (1.0 ml.) at room temperature for 16 hr. The stirred mixture was then slowly diluted with water (10 ml.), followed by methanol (5 ml.). The crystalline precipitate was filtered off, washed with water and dried to give the title compound (665 mg., 100%), m.p. 148.5°-150.5°.

Workup

  1. filtrationThe crystalline precipitate was filtered off
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-79c32ab4e62c4eab96bc2cca18b2e23b
Source dataset
uspto-grants-1976_09
Patent number
US03980681

Reaction notes

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