Potassium Carbonate → tert-Butyl [4-(cyanomethyl)phenoxy]acetate

HRID 1087005ノート

反応式

HRID 1087005 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.Br[CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:16]([O:15][C:13]([CH2:12][O:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1)=[O:14])([CH3:19])([CH3:18])[CH3:17]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 265484-Hydroxybenzyl cyanideHCID 79177tert-Butyl bromoacetate

生成物 1

HCID 15036608tert-Butyl [4-(cyanomethyl)phenoxy]acetate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 3 g of p-hydroxyphenylacetonitrile, 3.6 ml of t-butyl bromoacetate, 6.5 g of potassium carbonate in 45 ml of dimethylformamide is stirred at room temperature for 16 hours. After dilution with water the product is extracted with ether. The ether layer is washed with 1 N sodium hydroxide, dried over magnesium sulfate and the solvent removed in vacuo to yield p-(t-butoxycarbonylmethoxy)-phenylacetonitrile which is reduced to p-(t-butoxycarbonylmethoxy)-2-phenethylamine with sodium borohydride/cobalt chloride as described for the starting material under a).

後処理

  1. extractionAfter dilution with water the product is extracted with ether
  2. washThe ether layer is washed with 1 N sodium hydroxide
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent removed in vacuo

出典と根拠

ORDレコード
ord-dba0003d33434f5dace37f274d1eeb23
出典データセット
uspto-grants-1991_07
特許番号
US05034381

反応ノート

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