1,2-Dichloroethane → Ethyl 3-[(dipropylamino)carbonyl]-5-(hydroxymethyl)benzoate

HRID 348816

반응식

HRID 348816 반응식
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([CH2:15][OH:16])[CH:14]=1)[C:9]([OH:11])=O)=[O:5])[CH3:2].C(Cl)CCl.C(N(C(C)C)CC)(C)C.[CH2:30]([NH:33][CH2:34][CH2:35][CH3:36])[CH2:31][CH3:32]>CN(C=O)C>[CH2:30]([N:33]([CH2:34][CH2:35][CH3:36])[C:9]([C:8]1[CH:7]=[C:6]([CH:14]=[C:13]([CH2:15][OH:16])[CH:12]=1)[C:4]([O:3][CH2:1][CH3:2])=[O:5])=[O:11])[CH2:31][CH3:32]

참가 물질

6

반응물 4

HCID 111,2-DichloroethaneHCID 8902DipropylamineHCID 81531DiisopropylethylamineHCID 210858293-(Ethoxycarbonyl)-5-(hydroxymethyl)benzoic acid

생성물 1

HCID 21086103Ethyl 3-[(dipropylamino)carbonyl]-5-(hydroxymethyl)benzoate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of diethyl 1,3,5-benzenetricarboxylate (5.2 g) and borane methylsulfide complex (6.1 g) is stirred in THF (150 mL) at 20–25 degrees C. overnight. The mixture is then treated with methanol, concentrated to dryness, and chouromatographed (silica gel) to give diethyl 5-(hydroxymethyl)isophthalate. Diethyl 5-(hydroxymethyl)isophthalate (3.4 g) is hydroyzed in ethanol and water with lithium hydroxide monohydrate (0.57 g) at 20–25 degrees C. for 3.5 hours at which time the solvents are removed under reduced pressure. Water (100 mL) is added and the mixture is acidified to pH=4 with concentrated hydrochloric acid. The mixture is extracted with ethyl acetate and dried over magnesium sulfate, filtered, and concentrated to give 3-(ethoxycarbonyl)-5-(hydroxymethyl)benzoic acid, high resolution MS MH+=225.0769. 3-(Ethoxycarbonyl)-5-(hydroxymethyl)benzoic acid (2.3 g), EDC (3.0 g), 1-HOBT (2.1 g), diisopropylethylamine (2.7 mL), dipropyl amine (2.8 mL), and DMF (50 mL) are stirred at 20–25 degrees C. overnight. The mixture is then partitioned between ethyl acetate, water, and saline. The organic phase is separated and dried over magnesium sulfate, filtered, and concentrated. Chromatography (silica gel) gives ethyl 3-[(dipropylamino)carbonyl]-5-(hydroxymethyl)benzoate, NMR (CDCl3) δ 0.77, 1.0, 1.4, 1.6, 1.7, 3.2, 3.5, 4.4, 4.8, 7.6, 8.0 and 8.1.

후처리

  1. customovernight
  2. customThe mixture is then partitioned between ethyl acetate, water, and saline
  3. customThe organic phase is separated
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-7de29cef018b4d15b03a9b570188e3cd
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07176242B2

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