Dimethylformamide → HCID 86629083、化合物

HRID 500070

反応式

HRID 500070 の反応式
C[C:2]([CH3:5])([O-])[CH3:3].[K+].O=[C:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:10][CH2:9]1.[Cl-].[NH4+].[CH3:24]N(C)C=O>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)CCC>[CH:24](=[C:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:10][CH2:9]1)[CH2:3][CH2:2][CH3:5]

参加物

6

反応物 4

HCID 6228Dimethylformamide2 回HCID 25517Ammonium ChlorideHCID 1512535tert-butyl N-(4-oxocyclohexyl)carbamateHCID 23665647Potassium tert-butoxide

生成物 1

HCID 86629083HCID 86629083、化合物

試薬・触媒・溶媒 1

HCID 159628Butyltriphenylphosphonium bromide触媒

実験手順

To a mixture of potassium t-butoxide (2.05 g) and anhydrous N,N-dimethylformamide (60 ml) was added butyltriphenylphosphonium bromide (7.30 g) at room temperature. The mixture was stirred for 15 minutes and then a solution of t-butyl 4-oxocyclohexylcarbamate (1.30 g) in N,N-dimethylformamide (10 ml) was added to the mixture. The reaction mixture was stirred at room temperature overnight and then saturated aqueous ammonium chloride was added to the mixture. The mixture was extracted with toluene, and the organic layer was washed with brine, dried over sodium sulfate, and then the solvent was removed in vacuo. After diethyl ether was added to the residue, the precipitate was filtered off and then the filtrate was concentrated under reduced pressure. The residue was purified by a silica gel chromatography (eluent: gradient from 100% hexane/0% ethyl acetate to 0% hexane/100% ethyl acetate) to give 1.40 g of t-butyl (4-butylidenecyclohexyl)carbamate.

後処理

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. extractionThe mixture was extracted with toluene
  3. washthe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customthe solvent was removed in vacuo
  6. additionAfter diethyl ether was added to the residue
  7. filtrationthe precipitate was filtered off
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe residue was purified by a silica gel chromatography (eluent: gradient from 100% hexane/0% ethyl acetate to 0% hexane/100% ethyl acetate)

出典と根拠

ORDレコード
ord-1fa0f1a583cb4d2886f66a95cb1ac0bd
出典データセット
uspto-grants-2010_08
特許番号
US07767854B2

関連ノート

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