Dimethyl Sulfide → Methyl 2-({4-[3-(4-hydroxyphenoxy)propyl]phenoxy}methyl)benzoate

HRID 2112026

반응식

HRID 2112026 반응식
C([O:8][C:9]1[CH:36]=[CH:35][C:12]([O:13][CH2:14][CH2:15][CH2:16][C:17]2[CH:34]=[CH:33][C:20]([O:21][CH2:22][C:23]3[CH:32]=[CH:31][CH:30]=[CH:29][C:24]=3[C:25]([O:27][CH3:28])=[O:26])=[CH:19][CH:18]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.CSC.B(F)(F)F.CCOCC.CCOC(C)=O>ClCCl>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([O:13][CH2:14][CH2:15][CH2:16][C:17]2[CH:34]=[CH:33][C:20]([O:21][CH2:22][C:23]3[CH:32]=[CH:31][CH:30]=[CH:29][C:24]=3[C:25]([O:27][CH3:28])=[O:26])=[CH:19][CH:18]=2)=[CH:35][CH:36]=1

참가 물질

6

반응물 4

HCID 1068Dimethyl SulfideHCID 8000Boron trifluoride etherateHCID 8857Ethyl AcetateHCID 68869717Methyl 2-[(4-{3-[4-(benzyloxy)phenoxy]propyl}phenoxy)methyl]benzoate

생성물 1

HCID 68869776Methyl 2-({4-[3-(4-hydroxyphenoxy)propyl]phenoxy}methyl)benzoate수율 57.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Methyl 2-[(4-{3-[4(benzyloxy)phenoxy]propyl}phenoxy)methyl]benzoate (0.70 g, 1.45 mmol) was dissolved in dichloromethane (10 ml). Dimethylsulfide (1.08 g, 17.4 mmol) and borontrifluoride etherate (2.06 g, 14.5 mmol) was added and the mixture was stirred at room temperature for six hours. EtOAc (10 ml) was added and the organic phase was washed with water (3×10 ml), dried (MgSO4) and the solvent was removed by evaporation. The crude was purified by preparative HPLC (started with acetonitrile/buffer 60/40 and then the acetonitrile concentration was increased to 100%, the buffer was a mixture of acetonitrile/water 10/90 and ammonium acetate (0.1 M, column KR-100-7-C8, 50 mm×250 mm, flow 40 ml/min)). The product containing fractions were pooled and the acetonitrile was removed by evaporation. EtOAc (10 ml) was added and the organic phase was washed with two portions of brine and dried (MgSO4). After removing the solvent by evaporation 0.328 gram of methyl 2-({4-[3-(4-hydroxyphenoxy)propyl]-phenoxy}methyl)benzoate (yield 57.6%) was obtained.

후처리

  1. washthe organic phase was washed with water (3×10 ml)
  2. dry with materialdried (MgSO4)
  3. customthe solvent was removed by evaporation
  4. customThe crude was purified by preparative HPLC (
  5. concentrationthe acetonitrile concentration
  6. temperaturewas increased to 100%
  7. additiona mixture of acetonitrile/water 10/90 and ammonium acetate (0.1 M, column KR-100-7-C8, 50 mm×250 mm, flow 40 ml/min))
  8. additionThe product containing fractions
  9. customthe acetonitrile was removed by evaporation
  10. additionEtOAc (10 ml) was added
  11. washthe organic phase was washed with two portions of brine
  12. dry with materialdried (MgSO4)
  13. customAfter removing the solvent

출처 및 근거

ORD 기록
ord-ab7935c136134be4ab60bbeb9ec1e460
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07521461B2

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