Acetone → (2R)-3,4-Dihydro-2H-1-benzopyran-2-methanol

HRID 23330노트

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HRID 23330 반응식
[C:1]1([CH3:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:8]([OH:10])[CH3:9].[BH4-].[Na+].Cl.C[C:15](=[O:17])C>O>[O:10]1[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[CH2:7][CH2:9][C@@H:8]1[CH2:15][OH:17]

참가 물질

7

반응물 5

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 702EthanolHCID 1140TolueneHCID 4311764Sodium borohydride

생성물 1

HCID 7170029(2R)-3,4-Dihydro-2H-1-benzopyran-2-methanol

시약·촉매·용매 1

HCID 962Water용매

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온도
50 °C

실험 절차

A mixture of toluene (1000 ml) and ethanol (absolute, 520 ml) was stirred. Sodium borohydride (2.13 mol) was added at room temperature, under an inert atmosphere. The mixture was heated to 50° C. Intermediate (2) (2.14 mol) was added dropwise at 50° C. in a 90-minutes period (exothermic temperature rise of 15° C.; cooling required). The reaction mixture was stirred for 90 minutes at 50° C. Water (1500 ml) was added while stirring. Then, 2-propanone (100 ml) was added dropwise under slight cooling. The mixture was decomposed with HCl (180 ml). The organic layer was separated, dried, filtered and the solvent evaporated, yielding 295 g of (−)-(R)-3,4-dihydro-2H-1-benzopyran-2-methanol (interm. 3).

후처리

  1. temperature(exothermic temperature rise of 15° C.; cooling required)
  2. stirringThe reaction mixture was stirred for 90 minutes at 50° C
  3. stirringwhile stirring
  4. customThe organic layer was separated
  5. customdried
  6. filtrationfiltered
  7. customthe solvent evaporated

출처 및 근거

ORD 기록
ord-938e808cf9014a2ebe3a8bf8550e251e
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06852714B2

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