Benzyl Alcohol → Benzyl 4-fluorobenzoate

HRID 971178

反応式

HRID 971178 の反応式
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:9][C:10]1[CH:18]=[CH:17][C:13]([C:14](O)=[O:15])=[CH:12][CH:11]=1.C1(N=C=NC2CCCCC2)CCCCC1.C(OC(=O)C1C=CC=CC=1F)C1C=CC=CC=1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH2:1]([O:8][C:14](=[O:15])[C:13]1[CH:17]=[CH:18][C:10]([F:9])=[CH:11][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 244Benzyl AlcoholHCID 99734-Fluorobenzoic AcidHCID 10868DicyclohexylcarbodiimideHCID 5793312-Fluorobenzoic acid, benzyl ester

生成物 1

HCID 579322Benzyl 4-fluorobenzoate

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

Benzyl alcohol (4.05 mL, 39.1 mmol) was added slowly to a stirring solution of 4-fluorobenzoic acid (5.00 g, 35.7 mmol), 4-(dimethylamino)pyridine (432 mg, 3.53 mmol), and 1,3-dicyclohexylcarbodiimide (8.15 g, 39.5 mmol) in anhydrous CH2Cl2 at room temperature under an argon atmosphere. After 18 h the reaction was worked up according to procedures as outlined for the synthesis of 16. Flash chromatographic purification over silica (10% EtOAc in hexanes) afforded 17 as a clear, colorless liquid (7.75 g, 94%). 1H-NMR (500 MHz, CDCl3) δ 5.35 (s, 2H), 7.06-14 (m, 2H), 7.32-7.41 (m, 3H), 7.41-7.47 (m, 2H), 8.06-8.12 (m, 2H); 13C-NMR (125 MHz, CDCl3) δ 66.84, 115.5 (d, JC-F=22.0 Hz), 126.4 (d, JC-F=2.9 Hz), 128.2, 128.3, 128.6, 132.3 (d, JC-F=9.6 Hz), 135.9, 165.5, 165.8 (d, JC-F=253 Hz); GC-MS 230 m/z [M]+, C14H11OF2 requires 230.

後処理

  1. customFlash chromatographic purification over silica (10% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-a396c85958c94bddb6beda696e2d32d5
出典データセット
uspto-grants-2007_12
特許番号
US07312361B2

関連ノート

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