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

HRID 1595496ノート

反応式

HRID 1595496 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-00b9dcc3c5b844d1ac6c58706fa40799
出典データセット
uspto-grants-2001_09
特許番号
US06288096B1

反応ノート

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