(Dimethyl sulfide)trihydroboron → 2,3-Difluoro-4-(2-hydroxyethyl)phenol

HRID 1689396

반응식

HRID 1689396 반응식
CSC.B.[F:5][C:6]1[C:11]([F:12])=[C:10]([OH:13])[CH:9]=[CH:8][C:7]=1[CH2:14][C:15](O)=[O:16]>O1CCCC1>[F:12][C:11]1[C:6]([F:5])=[C:7]([CH2:14][CH2:15][OH:16])[CH:8]=[CH:9][C:10]=1[OH:13]

참가 물질

4

반응물 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 299221072-(2,3-Difluoro-4-hydroxyphenyl)acetic acid

생성물 1

HCID 534161452,3-Difluoro-4-(2-hydroxyethyl)phenol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of borane dimethylsulfide complex (2M in THF, 14.4 mL) was added dropwise to a solution of 2-(2,3-difluoro-4-hydroxyphenyl)acetic acid (example 77, step a) (1.08 g) in tetrahydrofuran (25 mL) at 0° C. and the resulting mixture was allowed to warm to RT and stirred overnight. The reaction was quenched with methanol and when bubbling had ceased the solvent evaporated. The residue was purified by silica gel chromatography eluting with 4:1 isohexane:ethyl acetate to ethyl acetate gradient. The fractions containing product were combined and evaporated to give the subtitled compound as white solid. Yield 0.95 g.

후처리

  1. customThe reaction was quenched with methanol and when
  2. custombubbling
  3. customevaporated
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with 4:1 isohexane
  6. additionThe fractions containing product
  7. customevaporated

출처 및 근거

ORD 기록
ord-4d3caea8e3284c38a3665431d788b75d
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148373B2

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