1-Chloro-3,4-dihydronaphthalene-2-carboxaldehyde → (1-Chloro-3,4-dihydronaphthalen-2-yl)methanol

HRID 330268

반응식

HRID 330268 반응식
[BH4-].[Na+].[Cl:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6][C:5]=1[CH:14]=[O:15]>CO.C1COCC1>[Cl:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6][C:5]=1[CH2:14][OH:15]

참가 물질

5

반응물 2

HCID 767521-Chloro-3,4-dihydronaphthalene-2-carboxaldehydeHCID 4311764Sodium borohydride

생성물 1

HCID 14819335(1-Chloro-3,4-dihydronaphthalen-2-yl)methanol수율 102.2%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

To a mixture of sodium borohydride (2.83 g, 0.075 mol) in methanol (150 mL) at 0° C., was added dropwise a solution of 1-chloro-2-formyl-3,4-dihydronaphthalene (9.59 g, 0.05 mol) in dry THF (150 mL). The reaction was stirred at room temperature for 1 hour, carbon dioxide was cautiously bubbled through the reaction mixture for 15 minutes, and the resulting mixture was concentrated under reduced pressure. The residue was diluted with water (150 mL), extracted with ether (3×150 mL), dried (MgSO4) and concentrated to give 9.95 g (102%) of product as a yellow oil.

후처리

  1. customcarbon dioxide was cautiously bubbled through the reaction mixture for 15 minutes
  2. concentrationthe resulting mixture was concentrated under reduced pressure
  3. additionThe residue was diluted with water (150 mL)
  4. extractionextracted with ether (3×150 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-a203c78374d04dca998de492e3dae3ff
출처 데이터셋
uspto-grants-1990_01
특허 번호
US04895860

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