Methyl Acetate → HCID 11066552, compound

HRID 1781578Notes

Reaction equation

HRID 1781578 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH:10]([CH2:13][OH:14])[CH2:11][OH:12])=[CH:4][CH:3]=1.[C:15](OC)(=[O:17])[CH3:16]>>[C:15]([O:14][CH2:13][C@@H:10]([CH2:11][OH:12])[CH2:9][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)(=[O:17])[CH3:16]

Participants

3

Reactant 2

HCID 6584Methyl AcetateHCID 10945134HCID 10945134, compound

Product 1

HCID 11066552HCID 11066552, compound

Procedure

To a solution of 4.6 g of 4-(4-bromophenyl)-2-(hydroxymethyl)butanol in 300 ml of methyl acetate was added 33.1 g of the above PPL preparation. The mixture was stirred while the progress of the reaction was monitored by HPLC method A. When the consumption of diol was complete, the mixture was immediately filtered and the filtrate was concentrated to an oil under vacuum. The oil was purified by flash chromatography on 200 g of silica with 3:1 ethyl acetate:hexane to obtain 4.82 g of the desired product as an oil. The 1-naphthyl carbamate derivative of a small portion of the product was prepared and analyzed by HPLC method B to determine that the product was 99% R and 1% S; the R isomer eluted at 9.4 minutes, and the S isomer at 12.6 minutes.

Workup

  1. custom33.1 g of the above PPL preparation
  2. customWhen the consumption of diol
  3. filtrationthe mixture was immediately filtered
  4. concentrationthe filtrate was concentrated to an oil under vacuum
  5. customThe oil was purified by flash chromatography on 200 g of silica with 3:1 ethyl acetate

Sources & evidence

ORD record
ord-f04f23e0e7f145c18e74c42a102f01f6
Source dataset
uspto-grants-1997_05
Patent number
US05633373

Reaction notes

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