Ethyl Acetate → 3-Benzyloxy-5-chlorobenzyl alcohol

HRID 2306177노트

반응식

HRID 2306177 반응식
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([Cl:18])[CH:17]=1)[C:12](O)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].CCOC(C)=O.[OH-].[Na+]>C1COCC1.O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([Cl:18])[CH:17]=1)[CH2:12][OH:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 108799093-(Benzoxy)-5-chlorobenzoic acidHCID 21226445Aluminium lithium hydride

생성물 1

HCID 110861343-Benzyloxy-5-chlorobenzyl alcohol

시약·촉매·용매 2

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매2회

실험 절차

To a stirred solution of 3-benzyloxy-5-chlorobenzoic acid, as described above in Step B, (5.0 g, 19 mmol) in dry THF (150 mL) at 0° C., under argon, was added LiAlH4 (29 mL of a 1.0 M solution in THF, 29 mmol) dropwise. The reaction mixture was stirred at ambient temperature for 3 hours, then EtOAc (1 mL) was added, followed by water (1 mL), then 15% aqueous NaOH (1 mL), then water (3 mL). The resulting mixture was filtered and concentrated in vacuo. The crude residue was purified by flash column chromatography on silica, eluting with hexane—20% EtOAc to yield the desired product as a colorless oil.

후처리

  1. filtrationThe resulting mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customThe crude residue was purified by flash column chromatography on silica
  4. washeluting with hexane—20% EtOAc

출처 및 근거

ORD 기록
ord-11ef5e2887164aa2a9bf698803f9befa
출처 데이터셋
uspto-grants-2002_08
특허 번호
US06441017B1

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