Grandlure II → (Z)-3-ethylidene-1,1-dimethylcyclohexane

HRID 374327

반응식

HRID 374327 반응식
[CH3:1][C:2]1([CH3:11])[CH2:7][CH2:6][CH2:5]/[C:4](=[CH:8]/[CH2:9]O)/[CH2:3]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1.[Cl-].[Cl-].[CH-]1C=CC=C1.[CH-]1C=CC=C1.[Ti+2]>[CH:8](=[C:4]1/[CH2:3][C:2]([CH3:11])([CH3:1])[CH2:7][CH2:6][CH2:5]/1)/[CH3:9]

참가 물질

5

반응물 2

HCID 5365896Grandlure IIHCID 21226445Aluminium lithium hydride

생성물 1

HCID 10351773(Z)-3-ethylidene-1,1-dimethylcyclohexane수율 84.8%

시약·촉매·용매 2

HCID 124040768Titanocene dichioride촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of 2.5 g of (Z)-2-(3,3-dimethyl-1-cyclohexylidene)-1-ethanol [see, for example, A. Gutmann et al., J. Chem. Ecology 7, 919 (1981)] in THF (tetrahydrofuran) was added dropwise, under stirring and argon, to a mixture of LiAlH4 (2 g) and titanocene dichloride (Fluka, 4 spatula tips) in absolute THF at -40°. The reaction mixture was left under stirring at room temperature during the weekend. After washing with water (2 ml), 15% NaOH (2 ml) and again water (6 ml) to hydrolyze, and filtering, 1.9 g of (Z)-3-ethylidene-1,1-dimethylcyclohexane were obtained and used as such in the following step. A small quantity of this product was bulb-to-bulb distilled for analysis:

후처리

  1. waitThe reaction mixture was left
  2. stirringunder stirring at room temperature during the weekend
  3. washAfter washing with water (2 ml), 15% NaOH (2 ml) and again water (6 ml)
  4. filtrationfiltering

출처 및 근거

ORD 기록
ord-009a1b406abb44ae8be412a5289270a7
출처 데이터셋
uspto-grants-1992_11
특허 번호
US05166412

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