Dimethyl Sulfide → 1-Chloro-3,7,11-trimethyldodeca-2,6,10-triene

HRID 374269

反応式

HRID 374269 の反応式
[Cl:1]N1C(=O)CCC1=O.CSC.[CH3:12][C:13]([CH2:17][CH2:18][CH:19]=[C:20]([CH3:28])[CH2:21][CH2:22][CH:23]=[C:24]([CH3:27])[CH2:25][CH3:26])=[CH:14]CO>ClCCl>[Cl:1][CH2:26][CH:25]=[C:24]([CH3:27])[CH2:23][CH2:22][CH:21]=[C:20]([CH3:28])[CH2:19][CH2:18][CH:17]=[C:13]([CH3:14])[CH3:12]

参加物

5

反応物 3

HCID 1068Dimethyl SulfideHCID 31398ChlorosuccinimideHCID 53916694HCID 53916694、化合物

生成物 1

HCID 40734091-Chloro-3,7,11-trimethyldodeca-2,6,10-triene収率 85%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

(Note all temperatures indicated are for the contents of the reaction flask). To a stirred solution of 299 mg (2.24 mmol) of N-chlorosuccinimide in 15 mL of dichloromethane at -30° C. under argon was added 0.18 mL (2.45 mmol) of distilled dimethyl sulfide over 5 minutes. After 10 minutes at -30° C., the reaction was allowed to warm to 0° C. for 10 minutes, followed by cooling to -40° C. A solution of 441.4 mg (1.99 mmol) of 3,7,11-trimethyl-2,6,10-tridecatrien-1-ol in 5 mL of dichloromethane was added dropwise over 10 minutes. The reaction was allowed to warm gradually to 0° C. over 1 hour, and then maintained at 0° C. for 1 hour. After quenching with cold water, the mixture was extracted with hexane and the hexane extract was washed with cold water and cold brine, dried (MgSO4) and evaporated to afford 483 mg of a crude product. Rapid flash chromatography on 20 g of Merck 9385 silica gel eluted with 3:97 ethyl acetate:petroleum ether provided 406.5 mg (85%) of a colorless liquid. 13C NMR indicated that this material contained a trace (3%) impurity.

後処理

  1. temperatureby cooling to -40° C
  2. temperatureto warm gradually to 0° C. over 1 hour
  3. temperaturemaintained at 0° C. for 1 hour
  4. customAfter quenching with cold water
  5. extractionthe mixture was extracted with hexane
  6. extractionthe hexane extract
  7. washwas washed with cold water and cold brine
  8. dry with materialdried (MgSO4)
  9. customevaporated
  10. customto afford 483 mg of a crude product
  11. washRapid flash chromatography on 20 g of Merck 9385 silica gel eluted with 3:97 ethyl acetate

出典と根拠

ORDレコード
ord-e862876f0adf45c28fec08c4415f3561
出典データセット
uspto-grants-1992_11
特許番号
US05166386

関連ノート

読み込み中…