Methanol → HCID 21904646, compound

HRID 1990730Notes

Reaction equation

HRID 1990730 reaction equation
C[O:2][C:3](=[O:18])[CH:4]([C:7]1[CH:12]=[C:11]([O:13][CH:14]([F:16])[F:15])[CH:10]=[C:9]([Cl:17])[CH:8]=1)[CH:5]=[O:6].CO.[BH4-].[Na+]>C1COCC1.C(OCC)(=O)C.O>[Cl:17][C:9]1[CH:8]=[C:7]([CH:12]=[C:11]([O:13][CH:14]([F:15])[F:16])[CH:10]=1)[CH:4]([CH2:5][OH:6])[C:3]([OH:18])=[O:2]

Participants

7

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 86614750HCID 86614750, compound

Product 1

HCID 21904646HCID 21904646, compoundYield 48.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

α-Formyl(3-chloro-5-difluoromethoxyphenyl)acetic acid methyl ester (400 mg, 1.4 mmol; see step (vii) above) was dissolved in THF:methanol (50 mL, 9:1). Sodium borohydride was added and the mixture was stirred at ambient temperature for 30 minutes. Water was added and the mixture was concentrated to produce an aqueous suspension, which was taken up in ethyl acetate and water. The phases were separated and the organic phase was washed with sodium chloride (15% in water), dried over sodium sulphate, filtered and concentrated at reduced pressure. The residue was dissolved in methanol (30 μL) and hydrolyzed with sodium hydroxide (1 mL, 10 M) at ambient temperature for 10 minutes. Extractive work up gave 180 mg, 0.68 mmol (yield: 48%) of the sub-title compound.

Workup

  1. concentrationthe mixture was concentrated
  2. customto produce an aqueous suspension, which
  3. customThe phases were separated
  4. washthe organic phase was washed with sodium chloride (15% in water)
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated at reduced pressure
  8. dissolutionThe residue was dissolved in methanol (30 μL) and hydrolyzed with sodium hydroxide (1 mL, 10 M) at ambient temperature for 10 minutes

Sources & evidence

ORD record
ord-3aa187905b2748d8aea3c4c52a01fe41
Source dataset
uspto-grants-2010_01
Patent number
US07645751B2

Reaction notes

Loading…