Water → HCID 178460514、化合物

HRID 726512

反応式

HRID 726512 の反応式
[C:1]1([C@H:7]2[CH2:12][CH2:11][C@H:10]([OH:13])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:14]1C[CH2:17][CH2:16][CH2:15]1.C(N(CC)CC)C.O>C(Cl)(=O)C=C.C1C=CC=CC=1>[C:15]([O:13][C@H:10]1[CH2:9][CH2:8][C@H:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:12][CH2:11]1)(=[O:14])[CH:16]=[CH2:17]

参加物

7

反応物 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 178521548HCID 178521548、化合物

生成物 1

HCID 178460514HCID 178460514、化合物収率 55.1%

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 13140Acryloyl chloride溶媒

実験手順

First, 2.5 g of trans-4-phenylcyclohexanol, 50 ml of tetrahydrofuran, and 1.8 g of triethylamine were placed in a 100 ml flask. A solution in which 1.7 g of acryloyl chloride was dissolved in 5 ml of benzene was added dropwise to the mixture under ice water cooling. The mixture was allowed to warm to room temperature and stirred for 5 hours. Water was added to the reaction mixture, and an organic layer was extracted with ether. The ether layer was washed with water and dried over anhydrous sodium sulfate. Thereafter, the solvent was distilled away. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=10/1) and recrystallized from acetone to obtain 1.8 g of trans-4-phenylcyclohexyl acrylate (Y: 55.1%). The compound thus obtained had a purity of 99.7% by GC and 1 spot by TLC. Furthermore, the compound had an m.p. of 67.3° C.

後処理

  1. additionwas added dropwise to the mixture under ice water cooling
  2. extractionan organic layer was extracted with ether
  3. washThe ether layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThereafter, the solvent was distilled away
  6. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=10/1)
  7. customrecrystallized from acetone

出典と根拠

ORDレコード
ord-2f59842550574b84b178087ad9bd6712
出典データセット
uspto-grants-1998_01
特許番号
US05709911

関連ノート

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