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

HRID 2053623

반응식

HRID 2053623 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-f2861f80ef71448e9b57d8d7df0715af
출처 데이터셋
uspto-grants-2008_02
특허 번호
US07326792B2

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