Cyclobutanecarboxylic acid, 3-ethyl- → 1-(3-Ethylcyclobutyl)ethanone

HRID 1252180

반응식

HRID 1252180 반응식
[CH2:1]([CH:3]1[CH2:6][CH:5]([C:7]([OH:9])=O)[CH2:4]1)[CH3:2].[CH3:10][Li]>CCOCC>[C:7]([CH:5]1[CH2:4][CH:3]([CH2:1][CH3:2])[CH2:6]1)(=[O:9])[CH3:10]

참가 물질

4

반응물 2

HCID 47796Cyclobutanecarboxylic acid, 3-ethyl-HCID 178418348HCID 178418348, 화합물

생성물 1

HCID 5377311-(3-Ethylcyclobutyl)ethanone

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

A solution of 6.61 g of 3-ethylcyclobutane-1-carboxylic acid, in 52 ml of distilled ether was stirred under argon at 0°. Methyllithium (85.0 ml of a 1.53M solution in ether) was added dropwise over a 30 minute period. The reaction mixture was stirred for three hours at 25°, then quenched with 7.3 water-methanol. The layers were separated, and the aqueous layer extracted with ether. The combined organic layers were washed with brine, dried, filtered and the solvents evaporated in vacuo. The resultant oil was distilled (aspirator vacuum) to afford 5.5 g of 1-acetyl-3-ethylcyclobutane, as a clear oil (bp 64°-67°). The material had the following spectral characteristics: nmr (CDCl3) δ 0.80 and 0.82 (3H total, pair of t, each J=7.0 Hz), 1.10 and 1.12 (ca. 1.5H total, pair of s, side product 1-[2-hydroxyprop-2-yl]-3-ethylcyclobutane), 1.0-2.4 (7H, m), 2.07 and 2.09 (3H total, pair of s) and 2.7-3.5 ppm and (1H, m); ir (CHCl3) 935, 1175, 1370, 1460, 1705, 2870, 2930 and 2970 cm-1, also small 3200-3600 broad and 3600 cm-1 for the side product noted above.

후처리

  1. customquenched with 7.3 water-methanol
  2. customThe layers were separated
  3. extractionthe aqueous layer extracted with ether
  4. washThe combined organic layers were washed with brine
  5. customdried
  6. filtrationfiltered
  7. customthe solvents evaporated in vacuo
  8. distillationThe resultant oil was distilled (aspirator vacuum)

출처 및 근거

ORD 기록
ord-721f23b6c6c14fa1b12412272929f9bb
출처 데이터셋
uspto-grants-1988_05
특허 번호
US04742080

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