Hydrochloric Acid → 1-Cyclopentyl-pent-4-yn-1-one

HRID 858868

반응식

HRID 858868 반응식
N1C=CC=CC=1S[C:8](=[O:13])[CH2:9][CH2:10][C:11]#[CH:12].[CH:14]1([Mg]Br)[CH2:18][CH2:17][CH2:16][CH2:15]1.Cl>C1COCC1>[CH:14]1([C:8](=[O:13])[CH2:9][CH2:10][C:11]#[CH:12])[CH2:18][CH2:17][CH2:16][CH2:15]1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 58762612Pent-4-ynethioic acid S-pyridin-2-yl EsterHCID 178419650HCID 178419650, 화합물

생성물 1

HCID 224997991-Cyclopentyl-pent-4-yn-1-one수율 99.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

To a solution of pent-4-ynethioic acid S-pyridin-2-yl ester (17.9 g, 94 mmol), dissolved in THF (900 mL) cooled to −78° C. was added cyclopentylmagnesium bromide (2.0 M, 94 mL, 188.5 mmol). The reaction was stirred for 15 minutes, and then warmed to −50° C. The reaction was poured into 500 mL 1 N HCl and the layers were separated. The aqueous layer was extracted with 2×200 mL diethyl ether and the organic layers were combined. The organics were then washed with 300 mL of 1 N NaOH. The organic layer was dried over Mg SO4, and the solids were removed by filtration. The solvent was removed by rotary evaporation to give the desired compound (14.0 g, 99% yield).

후처리

  1. temperaturewarmed to −50° C
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted with 2×200 mL diethyl ether
  4. washThe organics were then washed with 300 mL of 1 N NaOH
  5. dry with materialThe organic layer was dried over Mg SO4
  6. customthe solids were removed by filtration
  7. customThe solvent was removed by rotary evaporation

출처 및 근거

ORD 기록
ord-f920eae2f20c4242a34a21514f08dce6
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07148226B2

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