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

HRID 2399485ノート

反応式

HRID 2399485 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-93316fe2c4d44b1e9d6892c4331f1366
出典データセット
uspto-grants-1995_09
特許番号
US05449682

反応ノート

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