Sodium borohydride → 3,5-Dimethyl-4-(3'-iso-propyl-4'-methoxyphenoxy)benzyl alcohol

HRID 2108626노트

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HRID 2108626 반응식
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH3:22])[C:9]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([CH:19]([CH3:21])[CH3:20])[CH:12]=1)[CH:5]=[O:6].[BH4-].[Na+]>CO>[CH3:22][C:8]1[CH:7]=[C:4]([CH:3]=[C:2]([CH3:1])[C:9]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([CH:19]([CH3:20])[CH3:21])[CH:12]=1)[CH2:5][OH:6]

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 222856654-(3-Isopropyl-4-methoxy-phenoxy)-3,5-dimethyl-benzaldehyde

생성물 1

HCID 251506013,5-Dimethyl-4-(3'-iso-propyl-4'-methoxyphenoxy)benzyl alcohol수율 83%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a stirred solution of 3,5-dimethyl-4-(3′-iso-propyl-4′-methoxyphenoxy) benzaldehyde (4.1 g, 15.2 mmol, Example 28, step a) in methanol (35 mL) at 0° C. was slowly added NaBH4 (1.16 g, 30.5 mmol). The reaction mixture was stirred at room temperature for 5 h and the solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate (150 mL), washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel, eluting with ethyl acetate-hexanes (2:4) to afford 3,5-dimethyl-4-(3′-iso-propyl-4′-methoxyphenoxy)benzyl alcohol as a white solid (3.4 g, 83%, m.p.: 78-80° C.): 1H NMR (300 MHz, CDCl3): δ 7.12 (s, 2 H), 6.80 (d, J=3.3 Hz, 2 H), 6.67 (d, J=9.0 Hz, 1 H), 6.36 (dd, J=3.0, 8.7 Hz, 1 H), 4.68 (s, 2 H), 3.80 (s, 3 H), 3.35-3.25 (m, 1 H), 2.16 (s, 6 H), 1.19 (d, J=7.2 Hz, 6H); TLC conditions: Uniplate silica gel, 250 microns; mobile phase=ethyl acetate-hexanes (2:4); Rf=0.5.

후처리

  1. customat 0° C.
  2. customthe solvent was removed under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate (150 mL)
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by column chromatography on silica gel
  8. washeluting with ethyl acetate-hexanes (2:4)

출처 및 근거

ORD 기록
ord-ec2faf8a57104c33927ac2ad75e38b55
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07514419B2

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