Bromoethene → Nerolidol

HRID 436884노트

반응식

HRID 436884 반응식
[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]

참가 물질

5

반응물 3

HCID 11641BromoetheneHCID 1549778GeranylacetoneHCID 5462224Magnesium

생성물 1

HCID 5284507Nerolidol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  1. additionwas added dropwise

출처 및 근거

ORD 기록
ord-71632d25062341f0966dee5286df72d0
출처 데이터셋
uspto-grants-1977_06
특허 번호
US04028385

반응 노트

불러오는 중…