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

HRID 1174971ノート

反応式

HRID 1174971 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
120 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-953b68159630436fb3c650c97c7f6b4a
出典データセット
uspto-grants-2010_11
特許番号
US07838543B2

反応ノート

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