Sodium hydride → ethyl (RS)-4-(2-methoxycarbonyl-5-benzyloxyphenoxy)-4-phenylbutanoate

HRID 322877

반응식

HRID 322877 반응식
[H-].[Na+].[CH2:3]([O:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([OH:21])[CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[CH:23]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]>CN(C)C=O>[CH3:18][O:17][C:15]([C:14]1[CH:19]=[CH:20][C:11]([O:10][CH2:3][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)=[CH:12][C:13]=1[O:21][CH:23]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[O:16]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 225489Methyl 4-(benzyloxy)-2-hydroxybenzoateHCID 12847348Ethyl 4-chloro-4-phenylbutanoate

생성물 1

HCID 23204310ethyl (RS)-4-(2-methoxycarbonyl-5-benzyloxyphenoxy)-4-phenylbutanoate수율 57.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A stirred suspension of sodium hydride (340 mg) in dry dimethylformamide (100 mL) is treated portionwise with methyl 4-benzyloxy-2-hydroxybenzoate (2 g). After stirring at ambient temperature for 30 minutes, it is treated with ethyl (RS)-4-chloro-4-phenylbutanoate (1.9 g) in one portion and stirred for 16 hours at ambient temperature, and then for two hours at 80° C. The reaction mixture is then concentrated in vacuo and the residue is partitioned between ethyl acetate (100 mL) and water (100 mL). The organic layer is dried over magnesium sulphate, filtered and concentrated in vacuo. Flash chromatography of the resulting oil, eluting with 5-10% ethyl acetate/cyclohexane, affords ethyl (RS)-4-(2-methoxycarbonyl-5-benzyloxyphenoxy)-4-phenylbutanoate (2 g), in the form of a yellow oil.

후처리

  1. stirringstirred for 16 hours at ambient temperature
  2. waitfor two hours at 80° C
  3. concentrationThe reaction mixture is then concentrated in vacuo
  4. customthe residue is partitioned between ethyl acetate (100 mL) and water (100 mL)
  5. dry with materialThe organic layer is dried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. washFlash chromatography of the resulting oil, eluting with 5-10% ethyl acetate/cyclohexane

출처 및 근거

ORD 기록
ord-7554c6594e5140b6b1022816babaec49
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211234B1

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