Lithium borohydride → 2-Thiophenemethanol, 5-[4-(trifluoromethyl)phenyl]-

HRID 1785220

반응식

HRID 1785220 반응식
C[C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=2)[S:4][C:3]=1[CH:17]=[O:18].[Li+].[BH4-]>C1COCC1>[F:15][C:13]([F:14])([F:16])[C:10]1[CH:9]=[CH:8][C:7]([C:5]2[S:4][C:3]([CH2:17][OH:18])=[CH:2][CH:6]=2)=[CH:12][CH:11]=1

참가 물질

4

반응물 2

HCID 4148881Lithium borohydrideHCID 219865503-Methyl-5-[4-(trifluoromethyl)phenyl]thiophene-2-carbaldehyde

생성물 1

HCID 219863522-Thiophenemethanol, 5-[4-(trifluoromethyl)phenyl]-

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 3-methyl-5-(4-Trifluoromethyl-phenyl)-thiophene-2-carbaldehyde (0.140 g, 0.518 mmole) in THF (5 mL), is added to LiBH4 (0.056 g, 2.57 mmole) in one portion at 0° C. The reaction is kept at 0° C. for 15 minutes and warmed up to room temperature for 1 hour. The reaction is quenched using 1N HCl (10 mL) at 0° C. The THF is removed on rota vapor, the aqueous solution is then extracted with ethyl acetate (2×10 mL). The combined organic solution is washed with brine (3×20 mL), dried over Na2SO4 and concentrated. The crude product is purified on a silica gel column, eluting with 20% ethyl acetate in hexane and concentrated to provide the titled compound as white solid.

후처리

  1. customThe reaction is quenched
  2. customat 0° C
  3. customThe THF is removed on rota vapor
  4. extractionthe aqueous solution is then extracted with ethyl acetate (2×10 mL)
  5. washThe combined organic solution is washed with brine (3×20 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe crude product is purified on a silica gel column
  9. washeluting with 20% ethyl acetate in hexane
  10. concentrationconcentrated

출처 및 근거

ORD 기록
ord-f2d6a7054a7142a989ab67dc32fa753b
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07504433B2

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