Sodium borohydride → Methyl 2-(4-hydroxymethyl-2-methylphenoxy)phenylacetate

HRID 2255594노트

반응식

HRID 2255594 반응식
[CH:1]([C:3]1[CH:20]=[CH:19][C:6]([O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14][C:15]([O:17][CH3:18])=[O:16])=[C:5]([CH3:21])[CH:4]=1)=[O:2].[BH4-].[Na+]>CO>[OH:2][CH2:1][C:3]1[CH:20]=[CH:19][C:6]([O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14][C:15]([O:17][CH3:18])=[O:16])=[C:5]([CH3:21])[CH:4]=1

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 19385660Methyl 2-(4-formyl-2-methylphenoxy)phenylacetate

생성물 1

HCID 19385606Methyl 2-(4-hydroxymethyl-2-methylphenoxy)phenylacetate수율 66%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A stirred solution of 1.00 g (3.52 mmol) of the product of Step A dissolved in 14 mL of methanol was treated with 0.067 g (1.8 mmol) of sodium borohydride at room temperature. After 15 minutes the reaction mixture was partitioned between ethyl acetate and 1N hydrochloric acid, and the organic layer was separated. The product was washed with water, brine, dried (MgSO4), filtered and evaporated in vacuo. The residue was purified on a silica gel flash chromatography column eluted with 30% ethyl acetate/hexane to afford 0.660 g (66%) of the title compound.

후처리

  1. customAfter 15 minutes the reaction mixture was partitioned between ethyl acetate and 1N hydrochloric acid
  2. customthe organic layer was separated
  3. washThe product was washed with water, brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified on a silica gel flash chromatography column
  8. washeluted with 30% ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-fa32a5d0e0754492a1ae7f21cf8d1c01
출처 데이터셋
uspto-grants-1993_08
특허 번호
US05240938

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