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Sodium borohydride → Methyl [4-(5-hydroxy-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl)-phenyl]-acetate

HRID 24260
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HRID 24260 반응식
[CH3:1][C:2]1([CH3:26])[C:11]2[CH:10]=[C:9]([C:12]#[C:13][C:14]3[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23][CH3:24])=[O:22])=[CH:16][CH:15]=3)[CH:8]=[CH:7][C:6]=2[C:5](=[O:25])[CH2:4][CH2:3]1.[BH4-].[Na+]>CO>[CH3:24][O:23][C:21](=[O:22])[CH2:20][C:17]1[CH:16]=[CH:15][C:14]([C:13]#[C:12][C:9]2[CH:8]=[CH:7][C:6]3[CH:5]([OH:25])[CH2:4][CH2:3][C:2]([CH3:1])([CH3:26])[C:11]=3[CH:10]=2)=[CH:19][CH:18]=1
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참가 물질

4

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HCID 4311764Sodium borohydrideHCID 12971710Methyl [4-(8,8-dimethyl-5-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl-ethynyl)-phenyl]-acetate2회

생성물 1

HCID 86585937Methyl [4-(5-hydroxy-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl)-phenyl]-acetate수율 87%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
0 °C

실험 절차

To a solution of methyl [4-(8,8-dimethyl-5-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl-ethynyl)-phenyl]-acetate (Compound 4) in 5 mL MeOH at 0° C. was added NaBH4 (18.0 mg, 0.48 mmol). The reaction was stirred at 0° C. for 2 hours and then quenched by the addition of H2O. The solution was diluted with Et2O and washed with H2O and saturated aqueous NaCl before being dried (MgSO4) and the solvents were removed under reduced pressure. Column chromatography (20-40% EtOAc—hexanes) afforded 140.0 mg (87%) of the title compound as a colorless oil.

후처리

  1. customquenched by the addition of H2O
  2. additionThe solution was diluted with Et2O
  3. washwashed with H2O and saturated aqueous NaCl
  4. dry with materialbefore being dried (MgSO4)
  5. customthe solvents were removed under reduced pressure

출처 및 근거

ORD 기록
ord-3995de67c8474be3a2a7f36f1ca5b3b2
출처 데이터셋
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06855512B2

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