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

HRID 18832

반응식

HRID 18832 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 423677Acetic acid, rhodium salt (4:2)촉매HCID 8900Heptane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-610fe69eecf9401499714223ef20c5b1
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741493B2

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