Dichloromethane → [(1-Benzopyran-4-yloxy)methyl]acetic Acid Ethyl Ester

HRID 18832

反応式

HRID 18832 の反応式
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([OH:11])[CH2:3][CH2:2]1.[N+](=[CH:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N-].Cl[CH2:21]Cl>CCCCCCC.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[CH2:18]([O:17][C:15](=[O:16])[CH2:14][CH2:21][O:11][C:4]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=2[O:1][CH2:2][CH:3]=1)[CH3:19]

参加物

6

反応物 3

HCID 6344DichloromethaneHCID 12192Ethyl diazoacetateHCID 92890Chroman-4-ol

生成物 1

HCID 68569392[(1-Benzopyran-4-yloxy)methyl]acetic Acid Ethyl Ester

試薬・触媒・溶媒 2

HCID 423677Acetic acid, rhodium salt (4:2)触媒HCID 8900Heptane溶媒

実験手順

To a solution of 4-chromanol (1.5 g, 10.0 mmol) in dichloromethane (20 mL) is added rhodium (II) acetate dimer (10 mg) followed by ethyl diazoacetate (0.95 mL, 9.0 mmol). The reaction mixture is stirred at rt for 30 min. The reaction mixture is diluted with heptane, filtered through Celite, and the filtrate is evaporated and the residue purified by chromatography on silica gel; elution with EtOAc:dichloromethane:hexane (10:20:70) gives 1.81 g of the product 475. 1H NMR (CDCl3) δ 7.35 (dd, 1H), 7.22 (dt, 1H), 6.90 (t, 1H), 6.84 (d, 1H), 4.56 (m, 1H), 4.36 (dd, 1H), 4.29 (dd, 1H), 4.23 (q, 2H), 4.19 (s, 2H), 2.18 (m, 1H), 2.05 (m, 1H), 1.30 (t, 3H); MS: m/z 236 (M++1).

後処理

  1. filtrationfiltered through Celite
  2. customthe filtrate is evaporated
  3. customthe residue purified by chromatography on silica gel
  4. washelution with EtOAc:dichloromethane:hexane (10:20:70)

出典と根拠

ORDレコード
ord-610fe69eecf9401499714223ef20c5b1
出典データセット
uspto-grants-2010_06
特許番号
US07741493B2

関連ノート

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