Bromoethene → Nerolidol

HRID 436884ノート

反応式

HRID 436884 の反応式
[CH3:1][C:2]([CH3:14])=[CH:3][CH2:4][CH2:5]/[C:6](/[CH3:13])=[CH:7]/[CH2:8][CH2:9][C:10]([CH3:12])=[O:11].[Mg].[CH:16](Br)=[CH2:17]>O1CCCC1>[CH3:1][C:2]([CH3:14])=[CH:3][CH2:4][CH2:5]/[C:6](/[CH3:13])=[CH:7]/[CH2:8][CH2:9][C:10]([OH:11])([CH:16]=[CH2:17])[CH3:12]

参加物

5

反応物 3

HCID 11641BromoetheneHCID 1549778GeranylacetoneHCID 5462224Magnesium

生成物 1

HCID 5284507Nerolidol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

According to the method reported by A. Ofner et al. in Helv. Chim. Acta., 42 2577- 2584 (1959), cis- or trans-nerolidol was prepared respectively from cis- or trans-geranylacetone. That is, in 420 ml of tetrahydrofuran was placed 12.5 g of freshly-prepared metallic magnesium turnings and 60 g of vinyl bromide was added dropwise thereto under water cooling to form a Grignard reagent. 50 g cis- or trans-geranylacetone was added dropwise thereto at 25° C. The reaction mixture was neutralized with ammonium chloride and extracted with ether. The extract was dried over sodium sulfate and distilled off under reduced pressure. The residue was subjected to vacuum distillation to give cis-nerolidol from cis-geranylacetone in a yield of 82%. The product was identified by the standard product obtained in Example 12.

後処理

  1. additionwas added dropwise

出典と根拠

ORDレコード
ord-71632d25062341f0966dee5286df72d0
出典データセット
uspto-grants-1977_06
特許番号
US04028385

反応ノート

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