Acetic Anhydride → 3-Butylcyclohexanone

HRID 436537

반응식

HRID 436537 반응식
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH2:7]([Li])[CH2:8][CH2:9][CH3:10].[C:12]1(=[O:18])[CH2:17][CH2:16][CH2:15][CH:14]=[CH:13]1.[C:19](OC(=O)C)(=[O:21])[CH3:20]>CCOCC.CN(C)P(=O)(N(C)C)N(C)C>[CH2:3]([CH:2]1[CH2:15][CH2:14][CH2:13][C:12](=[O:18])[CH2:1]1)[CH2:4][CH2:5][CH3:6].[C:19]([CH:13]1[CH:14]([CH2:7][CH2:8][CH2:9][CH3:10])[CH2:15][CH2:16][CH2:17][C:12]1=[O:18])(=[O:21])[CH3:20]

참가 물질

8

반응물 4

HCID 7918Acetic AnhydrideHCID 8058HexaneHCID 135942-Cyclohexen-1-oneHCID 178418339Butyllithium

생성물 2

HCID 5661933-ButylcyclohexanoneHCID 11310101Cyclohexanone, 2-acetyl-3-butyl-

시약·촉매·용매 2

HCID 3283Diethyl Ether용매2회HCID 12679Hexamethylphosphoramide용매

실험 절차

In the same way as in Example 4, 12.8 ml (20 mmol) of a 15 % by weight hexane solution of n-butyllithium was reacted with 960 mg (10 mmol) of a solution of 960 mg (10 mmol) of 2-cyclohexenone in 10 ml of ether for one hour in the presence of 1.9 g (10 mmol) of cuprous iodide and 2.0 g (10 mmol) of tri-n-butylphosphone. Then, 5 ml of hexamethylphosphoric triamide was added, and the mixture stirred for about 10 minutes. Furthermore, a solution of 5.1 g (50 mmol) of acetic anhydride in 20 ml of ether was added, and the mixture was stirred for an additional 2.5 hours at room temperature. After the reaction, the reaction product was post-treated, extracted, washed, and dried in the same way as in Example 4 to afford 2.285 g of a crude product. The crude product was purified by column chromatography to afford 81 mg (0.5 mmol) of 3-n-butylcyclohexanone as a by-product in a yield of 5%, and 98 mg (0.5 mmol) of 2-acetyl-3-n-butylcyclohexanone as a product in a yield of 5%.

후처리

  1. stirringthe mixture was stirred for an additional 2.5 hours at room temperature
  2. customAfter the reaction
  3. additionthe reaction product was post-treated
  4. extractionextracted
  5. washwashed
  6. customdried in the same way as in Example 4
  7. customto afford 2.285 g of a crude product
  8. customThe crude product was purified by column chromatography

출처 및 근거

ORD 기록
ord-c8af1a5cb48c498b9785ffe72ab31187
출처 데이터셋
uspto-grants-1977_02
특허 번호
US04009196

연결된 노트

불러오는 중…