Dicyclohexylcarbodiimide → 4-Oxo-decanoic acid 3,7-dimethyl-oct-2,6-dienyl ester

HRID 841149

反応式

HRID 841149 の反応式
[O:1]=[C:2]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH2:3][CH2:4][C:5]([OH:7])=[O:6].[CH3:14][C:15](=[CH:17][CH2:18][CH2:19]/[C:20](=[CH:22]/[CH2:23]O)/[CH3:21])[CH3:16].C1(N=C=NC2CCCCC2)CCCCC1.N1(C2C=CN=CC=2)CCCC1>ClCCl>[CH3:21][C:20]([CH2:19][CH2:18][CH:17]=[C:15]([CH3:16])[CH3:14])=[CH:22][CH2:23][O:6][C:5](=[O:7])[CH2:4][CH2:3][C:2](=[O:1])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

参加物

6

反応物 4

HCID 10868DicyclohexylcarbodiimideHCID 755674-PyrrolidinopyridineHCID 5386474-Oxo capric acidHCID 637566Geraniol

生成物 1

HCID 539704894-Oxo-decanoic acid 3,7-dimethyl-oct-2,6-dienyl ester収率 218.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of 5.2 g 4-oxo-decanoic acid, 13.5 g geraniol, 17.5 g N,N′-dicyclohexyl-carbodiimide and 1.0 g 4-pyrrolidinopyridine in 250 ml of dichloromethane was stirred for 24 hours at room temperature. The precipitate was filtered off, the filtrate was diluted with ether, washed with aqueous hydrochloric acid, saturated NaHCO3 and brine. The organic phase was dried, filtered and evaporated to dryness. The resulting oil-cristall mixture was purified by chromatography to yield 19.7 g of a colourless oil.

後処理

  1. filtrationThe precipitate was filtered off
  2. additionthe filtrate was diluted with ether
  3. washwashed with aqueous hydrochloric acid, saturated NaHCO3 and brine
  4. customThe organic phase was dried
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe resulting oil-cristall mixture was purified by chromatography

出典と根拠

ORDレコード
ord-a7d181d12292442e96cf23e8a9f9a07b
出典データセット
uspto-grants-2002_04
特許番号
US06369248B1

関連ノート

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