Citric Acid → t-Butyl {2-chloro-5-[(1e)-3-hydroxy-1-propenyl]phenoxy}acetate

HRID 1352858Notes

Reaction equation

HRID 1352858 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:14](/[CH:17]=[CH:18]/[CH:19]=[O:20])=[CH:13][C:3]=1[O:4][CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[BH4-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1.CO>[Cl:1][C:2]1[CH:16]=[CH:15][C:14](/[CH:17]=[CH:18]/[CH2:19][OH:20])=[CH:13][C:3]=1[O:4][CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7]

Participants

6

Reactant 3

HCID 311Citric AcidHCID 4311764Sodium borohydrideHCID 86594024t-butyl {2-chloro-5-[(1E)-3-oxo-1-propenyl]phenoxy}acetate

Product 1

HCID 131726453t-Butyl {2-chloro-5-[(1e)-3-hydroxy-1-propenyl]phenoxy}acetate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of the compound (631 mg, 2.00 mmol) of Example 20-3 in tetrahydrofuran (4.0 ml) and methanol (2.0 ml) was stirred at ice cooling. Thereto was dropped an aqueous solution (0.20 ml) of sodium borohydride (38.0 mg, 1.00 mmol) under ice cooling and the mixture was stirred for 3 hour at the same temperature. Thereto was added 10% aqueous citric acid solution and the solution was extracted with ethyl acetate. The organic layer was washed with water, an aqueous saturated sodium hydrogencarbonate, solution and an aqueous saturated sodium chloride solution in the order, and dried over sodium sulfate. The solvent was removed to give the subject compound as a colorless oil (651 mg, quantitatively).

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialan aqueous saturated sodium hydrogencarbonate, solution and an aqueous saturated sodium chloride solution in the order, and dried over sodium sulfate
  4. customThe solvent was removed

Sources & evidence

ORD record
ord-afb14b4e072544cd849765528f1c38ef
Source dataset
uspto-grants-2007_05
Patent number
US07220773B2

Reaction notes

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