Water → HCID 58009652, 화합물

HRID 1009479노트

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HRID 1009479 반응식
[CH:1]([C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][CH:15]=1)[O:6][C@H:7]([CH3:12])[C:8]([O:10][CH3:11])=[O:9])=[O:2].[BH4-].[Na+].C(OCC)(=O)C.O>CO>[OH:2][CH2:1][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][CH:15]=1)[O:6][C@H:7]([CH3:12])[C:8]([O:10][CH3:11])=[O:9]

참가 물질

6

반응물 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 51556787HCID 51556787, 화합물

생성물 1

HCID 58009652HCID 58009652, 화합물

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

2.50 g of 3-hydroxybenzaldehyde, 2.77 g of methyl L-(−)-lactate, and 6.44 g of triphenylphosphine were dissolved in 25.0 mL of THF, and 22.2 mL of a 2.2 M diethyl azodicarboxylate/toluene solution was added thereto under ice-cooling, followed by stirring at room temperature overnight. To the reaction liquid was added an aqueous saturated sodium hydrogen carbonate solution, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:3 to 1:1) to obtain 1.67 g of methyl (2R)-2-(3-formylphenoxy)propionate. The obtained methyl (2R)-2-(3-formylphenoxy)propionate was dissolved in 33.3 mL of methanol, and 394 mg of sodium borohydride was added thereto under ice-cooling, followed by stirring for 30 minutes. To the reaction liquid were added ethyl acetate and water, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to obtain 1.68 g of methyl (2R)-2-[3-(hydroxymethyl)phenoxy]propionate.

후처리

  1. temperatureunder ice-cooling
  2. customTo the reaction liquid
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-9e8df525da3c419c8b81d39c936f44e1
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07973078B2

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