Aluminium lithium hydride → (4-Benzyloxy-6-fluoro-naphthalen-2-yl)-methanol

HRID 2363808노트

반응식

HRID 2363808 반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].C[O:8][C:9]([C:11]1[CH:20]=[C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([F:29])[CH:17]=2)[CH:12]=1)=O>C1COCC1>[CH2:22]([O:21][C:19]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([F:29])[CH:17]=2)[CH:12]=[C:11]([CH2:9][OH:8])[CH:20]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 593265854-Benzyloxy-6-fluoro-naphthalene-2-carboxylic acid methyl ester

생성물 1

HCID 59326474(4-Benzyloxy-6-fluoro-naphthalen-2-yl)-methanol수율 82.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a suspension of LiAlH4 (1.76 g, 46.4 mmol) in dry THF (20 mL) was added a solution of 4-benzyloxy-6-fluoro-naphthalene-2-carboxylic acid methyl ester (4.80 g, 15.5 mmol) in THF (30 mL) drop wise at 0° C. under nitrogen. The reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was quenched through the addition of an aqueous solution of HCl (50%; 50 mL) and the resulting mixture was filtered through a bed of celite. The filtrate was extracted with ethyl acetate (2×100 mL). The combined organic extracts were washed with water (30 mL) followed by brine (30 mL), dried and concentrated in vacuo to obtain (4-benzyloxy-6-fluoro-naphthalen-2-yl)-methanol (3.6 g, 82.2%). The crude product was pure enough to proceed to the next step without further purification.

후처리

  1. customThe reaction mixture was quenched through the addition of an aqueous solution of HCl (50%; 50 mL)
  2. filtrationthe resulting mixture was filtered through a bed of celite
  3. extractionThe filtrate was extracted with ethyl acetate (2×100 mL)
  4. washThe combined organic extracts were washed with water (30 mL)
  5. customdried
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-8e6e7b4ac87b4217970df6a0cc761ae5
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08691993B2

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