Methanol → 4-(Hydroxymethyl)tetrahydro-2H-pyran-4-carbonitrile

HRID 1186428노트

반응식

HRID 1186428 반응식
[C:1]([C:3]1([C:9](OC)=[O:10])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1)#[N:2].CO.O.[BH4-].[Na+]>O1CCCC1.C(OCC)(=O)C>[C:1]([C:3]1([CH2:9][OH:10])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1)#[N:2]

참가 물질

7

반응물 4

HCID 887MethanolHCID 962Water2회HCID 4311764Sodium borohydrideHCID 16726727Methyl 4-cyanooxane-4-carboxylate

생성물 1

HCID 249369984-(Hydroxymethyl)tetrahydro-2H-pyran-4-carbonitrile수율 92%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

Methyl 4-cyanotetrahydro-2H-pyran-4-carboxylate (2.93 g, 17.3 mmol) was dissolved in tetrahydrofuran (50 mL), methanol (10 mL) and water (5.0 mL). To this, sodium borohydride (1.31 g, 34.6 mmol) was added and the mixture was stirred at room temperature for 30 minutes. The reaction was stopped by addition of water to the reaction mixture, and extraction with ethyl acetate was performed, followed by washing with brine and drying over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate) to give 4-cyanotetrahydro-2H-pyran-4-ylmethanol (1.59 g, yield: 92%).

후처리

  1. washby washing with brine
  2. dry with materialdrying over anhydrous sodium sulfate
  3. customThe solvent was evaporated off under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (ethyl acetate)

출처 및 근거

ORD 기록
ord-e0a4dcaf845e4ea990aabfca7bdeca90
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08673908B2

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