4-tert-Butylcyclohexanone → Cyclohexane, 1-(1,1-dimethylethyl)-4-methylene-

HRID 525445노트

반응식

HRID 525445 반응식
[Li][CH2:2]CCC.[C:6]([CH:10]1[CH2:15][CH2:14][C:13](=O)[CH2:12][CH2:11]1)([CH3:9])([CH3:8])[CH3:7]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[C:6]([CH:10]1[CH2:15][CH2:14][C:13](=[CH2:2])[CH2:12][CH2:11]1)([CH3:9])([CH3:8])[CH3:7]

참가 물질

5

반응물 2

HCID 73924-tert-ButylcyclohexanoneHCID 178418339Butyllithium

생성물 1

HCID 139425Cyclohexane, 1-(1,1-dimethylethyl)-4-methylene-수율 52.5%

시약·촉매·용매 2

HCID 74505Methyltriphenyliphosphonium bromide촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of methyltriphenylphosphonium bromide (5.36 g, 15 mmol, 1.5 eq) in dried THF (40 mL) was added n-BuLi (2.5 M) (6 mL, 15 mmol, 1.5 eq) at −78° C. The mixture was stirred at room temperature for 1 h. The solution of 4-tert-butylcyclohexanone (1.54 g, 10 mmol) in THF (10 mL) was added to the reaction mixture at −78° C. The mixture was stirred at 70° C. for 12 h. The solvent was removed and the residue was suspended in hexane. The mixture was filtered, and the filtrate was concentrated to give 1-tert-butyl-4-methylenecyclohexane as yellow oil (0.80 g, yield: 50%). 1HNMR (400 MHz, CDCl3) δ: 4.58 (s, 2H), 2.34-2.31 (m, 2H), 2.01-1.95 (m, 2H), 1.88-1.84 (m, 2H), 1.14-1.06 (m, 3H), 0.86 (s, 9H).

후처리

  1. stirringThe mixture was stirred at 70° C. for 12 h
  2. customThe solvent was removed
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated

출처 및 근거

ORD 기록
ord-ea09239368c040bf93b46c02c573f6fc
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340527B2

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