Triethylamine → 4-(cyclopent-1-en-1-yl)benzoic acid

HRID 1174971노트

반응식

HRID 1174971 반응식
I[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[CH:11]1[CH2:15][CH2:14][CH2:13][CH:12]=1.CCN(CC)CC.CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C1(C)C=CC=CC=1.CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:11]1([C:2]2[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=2)[CH2:15][CH2:14][CH2:13][CH:12]=1

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 8882CyclopenteneHCID 120854-Iodobenzoic acidHCID 80271Tri-o-tolylphosphine

생성물 1

HCID 2779144-(cyclopent-1-en-1-yl)benzoic acid수율 69.3%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

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온도
120 °C

실험 절차

In a sealed tube is added 4-iodobenzoic acid (5.0 g, 20.16 mmol), cyclopentene (17.8 mL, 2101.6 mmol), Et3N (8.4 mL, 60.48 mmol) in toluene (100 mL). It is purged with N2 for 15 min. Pd(OAc)2 (0.23 g, 1.01 mmol) and P(o-Tol)3 (0.61 g, 2.01 mmol) are added. The reaction is stirred at 120° C. overnight. It is diluted with EtOAc, washed with 1M HCl, H2O, and brine. Purification of the crude material by chromatography gives the title compound (2.63 g, 69%).

후처리

  1. customIt is purged with N2 for 15 min
  2. washwashed with 1M HCl, H2O, and brine
  3. customPurification of the crude material by chromatography

출처 및 근거

ORD 기록
ord-953b68159630436fb3c650c97c7f6b4a
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07838543B2

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