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Dimethylformamide → Di-tert-butyl (2-formyl-1,4-phenylene)dicarbamate

HRID 392006
ノート
印刷プレビュー

反応式

HRID 392006 の反応式
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[CH:11][C:10]=1Br)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[Li].C([Li])(C)(C)C.CN(C)[CH:33]=[O:34]>O.CCOCC>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[CH:11][C:10]=1[CH:33]=[O:34])([CH3:4])([CH3:3])[CH3:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 154289672,5-Bis-tert.-butyloxycarbonylaminobromobenzeneHCID 178418306HCID 178418306、化合物HCID 178418348HCID 178418348、化合物

生成物 1

HCID 15539052Di-tert-butyl (2-formyl-1,4-phenylene)dicarbamate

試薬・触媒・溶媒 2

HCID 962Water溶媒
2 回
HCID 3283Diethyl Ether溶媒

反応条件

温度
-20 °C

実験手順

3.3 g (0.01 mol) 2,5-bis-tert.-butyloxycarbonylaminobromobenzene from step A are dissolved in 100 ml of water-free tetrahydrofuran under argon. 17 ml of a 1.6 molar etheric methyl lithium solution (0.03 mol) are gradually added. The reaction mixture is cooled to −20° C., 7 ml of a 1.5 molar tert.-butyl lithium solution (0.01 mol) are gradually added. After the addition has ended the solution is stirred for 30 minutes at the given temperature. Subsequently 1.2 g of dimethyl formamide (0.02 mol) are added and the reaction mixture is stirred for one hour at −20° C. After slowly heating to room temperature the reaction mixture is hydrolyzed with water and then poured into ether, the aqueous phase is extracted with ether and then the organic phase is dried over magnesium sulfate. The solvent is distilled away in a rotary evaporator and the residue is purified on silica gel with a petroleum ether/ethyl acetate solvent (9/1).

後処理

  1. additionAfter the addition
  2. stirringthe reaction mixture is stirred for one hour at −20° C
  3. temperatureAfter slowly heating to room temperature the reaction mixture
  4. extractionthe aqueous phase is extracted with ether
  5. dry with materialthe organic phase is dried over magnesium sulfate
  6. distillationThe solvent is distilled away in a rotary evaporator
  7. customthe residue is purified on silica gel with a petroleum ether/ethyl acetate solvent (9/1)

出典と根拠

ORDレコード
ord-06234f2939e34f27afc0a33a3ff0805f
出典データセット
uspto-grants-2004_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06800097B2

反応ノート

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