4-Hydroxybenzaldehyde → tert-butyl N-{4-[2-(4-formylphenoxy)ethyl]phenyl}carbamate

HRID 1595496

반응식

HRID 1595496 반응식
[N+](C1C=C(S([O:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[CH:18][CH:17]=2)(=O)=O)C=CC=1)([O-])=O.O[C:31]1[CH:38]=[CH:37][C:34]([CH:35]=[O:36])=[CH:33][CH:32]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH:35]([C:34]1[CH:37]=[CH:38][C:31]([O:13][CH2:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([NH:22][C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[CH:20][CH:21]=2)=[CH:32][CH:33]=1)=[O:36]

참가 물질

5

반응물 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 545354424-(Tert-butoxycarbonylamino)phenethyl 3-nitro-benzenesulfonate

생성물 1

HCID 21704970tert-butyl N-{4-[2-(4-formylphenoxy)ethyl]phenyl}carbamate수율 79%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

26.7 g (63 mmole) 4-(tert-butoxycarbonylamino)phenethyl 3-nitro-benzenesulfonate, 8.5 g (69 mmole) p-hydroxybenzaldehyde, 9.54 g (69 mmole) potassium carbonate and acetonitrile was refluxed for 3 hours and thereafter stirred over night at room temperature. The precipitate was filtered off and the solvent was evaporated. Dichloromethane was added and the organic phase was washed with saturated sodium carbonate and thereafter with sodium hydroxide (0.1 M), dried (sodium sulfate), filtered and the solvent was evaporated to give 17 g (yield 79%) of tert-butyl N-{4-[2-(4-formylphenoxy)ethyl]phenyl}carbamate.

후처리

  1. filtrationThe precipitate was filtered off
  2. customthe solvent was evaporated
  3. additionDichloromethane was added
  4. washthe organic phase was washed with saturated sodium carbonate
  5. dry with materialwith sodium hydroxide (0.1 M), dried (sodium sulfate)
  6. filtrationfiltered
  7. customthe solvent was evaporated

출처 및 근거

ORD 기록
ord-00b9dcc3c5b844d1ac6c58706fa40799
출처 데이터셋
uspto-grants-2001_09
특허 번호
US06288096B1

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