Water → HCID 21864426, compound

HRID 622617Notes

Reaction equation

HRID 622617 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH2:10]>N1C=CC=CC=1.CCOCC>[C:1]([O-:8])(=[O:10])[CH3:2].[C:1]([O-:8])(=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 962WaterHCID 7412Benzoyl chloride

Product 1

HCID 21864426HCID 21864426, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Procedure

The 1α-hydroxy-38-triethylsilyloxy-compound from Example 9(b) (2 g) was treated with benzoyl chloride (2 ml) in pyridine (25 ml). After 30 min water was added and the mixture diluted with ether. After acid work-up, the solvent was removed and the resulting oil stirred overnight in THF:H2O: AcOH; 8:1:3 (36 ml). After dilution with ether and aqueous work-up, the crude benzoate-alcohol was taken up in benzene (40 ml). Triethylamine (7 ml), acetic anhydride (3 ml) and 4-dimethylaminopyridine (15 mg) were added. After 30 min, water was added and the mixture diluted with ether. Acid work-up and chromatography through silica (10 g) gave 1.76 g 83%) of the title acetate-benzoate as an oil. 1Hnmr δ 8.05 (m. W=12 Hz, 2H, aryl), 7.5 (m, W=10 Hz, 3H, aryl), 6.58 (d, J=11 Hz, C-6H), 5.88 (m, W=16 Hz, C-1H, 7H), 5.15 (m, W=10 Hz, C-3H, 19H2, 22H, 23H), 2.05 (s, OAc), 0.57 (s, C-18H3).

Workup

  1. customAfter acid work-up, the solvent was removed
  2. additionTriethylamine (7 ml), acetic anhydride (3 ml) and 4-dimethylaminopyridine (15 mg) were added
  3. waitAfter 30 min
  4. additionwater was added
  5. additionthe mixture diluted with ether

Sources & evidence

ORD record
ord-79a8e48dca8b43c19be428aab6057bfa
Source dataset
uspto-grants-1988_09
Patent number
US04772433

Reaction notes

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