Water → (2RS,3SR)-2-acetoxy-3-(3-benzyloxy-4-phenoxyphenyl)-5-phenylpentane

HRID 849369Notes

Reaction equation

HRID 849369 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:16]([CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:17]([OH:19])[CH3:18])[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(O[C:32](=[O:34])[CH3:33])(=O)C.CN([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40]N=1)C.O.N1C=CC=C[CH:46]=1>>[C:32]([O:19][CH:17]([CH:16]([C:5]1[CH:6]=[CH:7][C:8]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:3]([O:2][CH2:1][C:40]2[CH:46]=[CH:38][CH:43]=[CH:42][CH:41]=2)[CH:4]=1)[CH2:20][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[CH3:18])(=[O:34])[CH3:33]

Participants

6

Reactant 5

HCID 962WaterHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 218852-DimethylaminopyridineHCID 19591621(2RS,3SR)-3-(3-methoxy-4-phenoxyphenyl)-5-phenylpentan-2-ol

Product 1

HCID 19591477(2RS,3SR)-2-acetoxy-3-(3-benzyloxy-4-phenoxyphenyl)-5-phenylpentane

Procedure

380 mg of (2RS,3SR)-3-(3-methoxy-4-phenoxyphenyl)-5-phenylpentan-2-ol as an intermediate of Example 54(4), was dissolved in 5 ml of pyridine, and 1 ml of acetic anhydride and then 10 mg of dimethylaminopyridine were added, followed by stirring at room temperature for 30 minutes. The reaction solution was poured into water and extracted with ethyl ether. Then, the extract solution was sequentially washed with 1N hydrochloric acid, a saturated sodium hydrogen carbonate aqueous solution and a saturated sodium chloride aqueous solution, and then dried over anhydrous sodium sulfate. The drying agent was filtered off, and then, the solvent was distilled off under reduced pressure to obtain 466 mg (yield: quantitative) of the above identified compound as a colorless oily substance.

Workup

  1. extractionextracted with ethyl ether
  2. washThen, the extract solution was sequentially washed with 1N hydrochloric acid
  3. dry with materiala saturated sodium hydrogen carbonate aqueous solution and a saturated sodium chloride aqueous solution, and then dried over anhydrous sodium sulfate
  4. filtrationThe drying agent was filtered off
  5. distillationthe solvent was distilled off under reduced pressure
  6. customto obtain 466 mg (yield: quantitative) of the

Sources & evidence

ORD record
ord-5674698faf5d4993a8f63e1e9a90d4a3
Source dataset
uspto-grants-2000_01
Patent number
US06011174

Reaction notes

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