Tributylphosphine → Ethyl{2-methyl-4-[({5-[4-(trifluoromethyl)phenyl]-3-furyl}methyl)thio]phenoxy}acetate

HRID 9689

반응식

HRID 9689 반응식
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][CH:12]=[C:11]([CH2:14]O)[CH:10]=2)=[CH:5][CH:4]=1.C(P(CCCC)CCCC)CCC.[CH2:31]([O:33][C:34](=[O:45])[CH2:35][O:36][C:37]1[CH:42]=[CH:41][C:40]([SH:43])=[CH:39][C:38]=1[CH3:44])[CH3:32]>O1CCCC1>[CH2:31]([O:33][C:34](=[O:45])[CH2:35][O:36][C:37]1[CH:42]=[CH:41][C:40]([S:43][CH2:14][C:11]2[CH:10]=[C:9]([C:6]3[CH:7]=[CH:8][C:3]([C:2]([F:17])([F:16])[F:1])=[CH:4][CH:5]=3)[O:13][CH:12]=2)=[CH:39][C:38]=1[CH3:44])[CH3:32]

참가 물질

5

반응물 3

HCID 13831TributylphosphineHCID 16641178Ethyl (4-mercapto-2-methylphenoxy)acetateHCID 21986330{5-[4-(Trifluoromethyl)phenyl]-3-furyl}methanol

생성물 1

HCID 21986477Ethyl{2-methyl-4-[({5-[4-(trifluoromethyl)phenyl]-3-furyl}methyl)thio]phenoxy}acetate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of {5-[4-(trifluoromethyl)phenyl]-3-furyl}methanol (0.15 g) in tetrahydrofuran (15 ml) stirred at 0° C. was treated with tributylphosphine (0.2 ml), as solution of ethyl(4-mercapto-2-methylphenoxy)acetate (0.150 g) in tetrahydrofuran (2 ml) and finally azodicarbonyldimorpholide (0.204 g). The reaction was allowed to warm to ambient temperature and stirred for 18 hours. The solvent was evaporated and the residue subjected to an aqueous work up using ethyl acetate and water. The organic phase was dried over magnesium sulfate. The product isolated after evaporation of the solvent was further purified by flash column chromatography using a cyclohexane:ethyl acetate (5:1) as eluent to give the title compound.

후처리

  1. customThe solvent was evaporated
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. customThe product isolated
  4. customafter evaporation of the solvent
  5. customwas further purified by flash column chromatography

출처 및 근거

ORD 기록
ord-e19001d0595c45359652e9e2aef71108
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091237B2

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