Methanol → HCID 22664985, compound

HRID 392593Notes

Reaction equation

HRID 392593 reaction equation
[CH3:1][C:2]([C:9](=[O:17])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[Cl:16])([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].CO>O>[Cl:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[CH:9]([OH:17])[C:2]([CH3:8])([CH3:1])[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

4

Reactant 2

HCID 887MethanolHCID 22664966HCID 22664966, compound

Product 1

HCID 22664985HCID 22664985, compoundYield 81.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

tBuBisP*-RuBr2 (5 mg) was placed in a pressurized hydrogenation reactor equipped with a stirrer chip, and after deaeration, substituted with argon. Thereto was poured a mixture of deaerated ethyl 2,2-dimethyl(2-chlorobenzoyl)acetate (515 mg) (2.0 mmol), methanol (4 ml) and water (0.4 ml). The mixture was stirred under a hydrogen pressure (6 atm) at 70° C. for 24 h. According to the high performance liquid chromatography analysis of the mixture after completion of the reaction, the yield was 97% and enantioselectivity was 90% ee. After the analysis, the reaction mixture was concentrated to dryness and purified by column chromatography (hexane:ethyl acetate=3:1, silica gel: 50 g) to give the title compound (420 mg, 81.8%) as a colorless oil.

Workup

  1. customequipped with a stirrer chip
  2. additionThereto was poured
  3. customafter completion of the reaction
  4. concentrationAfter the analysis, the reaction mixture was concentrated to dryness
  5. custompurified by column chromatography (hexane:ethyl acetate=3:1, silica gel: 50 g)

Sources & evidence

ORD record
ord-9f4bf5fe0c264dc88b2904be92b107b6
Source dataset
uspto-grants-2004_10
Patent number
US06800778B1

Reaction notes

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