tert-Butanol → 1-(1,1-Dimethylethyl) 6-methyl hexanedioate

HRID 63400

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HRID 63400 반응식
[CH3:1][O:2][C:3](=[O:11])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9].C1N=CN(C(N2C=NC=C2)=O)C=1.[C:24](O)([CH3:27])([CH3:26])[CH3:25].C1CCN2C(=NCCC2)CC1>CN(C=O)C.CCOCC>[CH3:1][O:2][C:3](=[O:11])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]([O:10][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:9]

참가 물질

7

반응물 4

HCID 6386tert-ButanolHCID 12328monoMethyl adipateHCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

생성물 1

HCID 184750351-(1,1-Dimethylethyl) 6-methyl hexanedioate수율 78.6%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

반응 조건

온도
40 °C

실험 절차

To a solution of adipic acid monomethyl ester (4.8 g, 30 mmol) in DMF (30 mL), was added CDI (4.9 g, 30 mmol), and the resulting mixture was stirred under N2 at 40° C. for 1 hour. t-Butanol (4.4 g, 60 mmol) and DBU (4.6 g, 30 mmol) were added, and stirring proceeded at 40° C. for 70 hours. The mixture was poured into ether (100 mL), and this mixture was washed with 10% aq. HOAc (100 mL), 10% aq. K2CO3 (100 mL), and water (3×100 mL), dried (MgSO4), and evaporated, providing 5.1 g of hexanedioic acid tert-butyl ester methyl ester, in 78% yield; 1H NMR (CDCl3) δ 1.44 (s, 9H), 1.59-1.67 (m, 4H), 2.21-2.26 (m, 2H), 3.67 (s, 3H).

후처리

  1. stirringstirring
  2. waitproceeded at 40° C. for 70 hours
  3. washthis mixture was washed with 10% aq. HOAc (100 mL), 10% aq. K2CO3 (100 mL), and water (3×100 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated

출처 및 근거

ORD 기록
ord-a3d7ecaa7a4d404f803092b5cb53b354
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447070B2

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