Aluminium lithium hydride → (4-Benzyloxy-6-fluoro-3-methyl-naphthalen-2-yl)-methanol

HRID 1261428노트

반응식

HRID 1261428 반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].C[O:8][C:9]([C:11]1[C:20]([CH3:21])=[C:19]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([F:30])[CH:17]=2)[CH:12]=1)=O>C1COCC1>[CH2:23]([O:22][C:19]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([F:30])[CH:17]=2)[CH:12]=[C:11]([CH2:9][OH:8])[C:20]=1[CH3:21])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 593266024-Benzyloxy-6-fluoro-3-methyl-naphthalene-2-carboxylic acid methyl ester

생성물 1

HCID 59326595(4-Benzyloxy-6-fluoro-3-methyl-naphthalen-2-yl)-methanol수율 92.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a suspension of LiAlH4 (8.8 g, 235 mmol) in dry THF (120 mL) was added a solution of 4-benzyloxy-6-fluoro-3-methyl-naphthalene-2-carboxylic acid methyl ester (25.4 g, 78.4 mmol) in THF (180 mL) dropwise at 0° C. under nitrogen. The reaction mixture was stirred at room temperature for 3 hours. After this time, the reaction mixture was cooled to 0° C. and quenched carefully via addition of cold water (10 mL) followed by 15% NaOH solution (10 mL) and additional water. The resulting solution was stirred for one hour, then filtered through a sintered glass funnel. The filter pad was washed with THF (50 mL). The combined filtrates were dried over Na2SO4, filtered, and concentrated to afford (4-benzyloxy-6-fluoro-3-methyl-naphthalen-2-yl)-methanol (21.5 g, 92%, crude) as a white solid. The crude product was used in the next step without further purification. MS cald. for C19H16FO2 [(M−H)+]: 295, obsd. 294.9.

후처리

  1. temperatureAfter this time, the reaction mixture was cooled to 0° C.
  2. customquenched carefully via addition of cold water (10 mL)
  3. stirringThe resulting solution was stirred for one hour
  4. filtrationfiltered through a sintered glass funnel
  5. washThe filter pad was washed with THF (50 mL)
  6. dry with materialThe combined filtrates were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-4f762ab74596401895b50ffe650c4de8
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08470884B2

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