Triphenylphosphine → {4-[3,3-Bis-(3-methyl-thiophen-2-yl)-allylsulfanyl]-2-trifluoromethyl-phenoxy}-acetic acid ethyl ester

HRID 1247685ノート

反応式

HRID 1247685 の反応式
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([C:11]1[S:12][CH:13]=[CH:14][C:15]=1[CH3:16])=[CH:8][CH2:9]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[CH2:48]([O:50][C:51](=[O:65])[CH2:52][O:53][C:54]1[CH:59]=[CH:58][C:57]([SH:60])=[CH:56][C:55]=1[C:61]([F:64])([F:63])[F:62])[CH3:49]>C1COCC1>[CH2:48]([O:50][C:51](=[O:65])[CH2:52][O:53][C:54]1[CH:59]=[CH:58][C:57]([S:60][CH2:9][CH:8]=[C:7]([C:11]2[S:12][CH:13]=[CH:14][C:15]=2[CH3:16])[C:3]2[S:4][CH:5]=[CH:6][C:2]=2[CH3:1])=[CH:56][C:55]=1[C:61]([F:62])([F:63])[F:64])[CH3:49]

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 219076783,3-Bis-(3-methylthiophen-2-yl)-prop-2-en-1-olHCID 59516001Ethyl [4-sulfanyl-2-(trifluoromethyl)phenoxy]acetate

生成物 1

HCID 68575646{4-[3,3-Bis-(3-methyl-thiophen-2-yl)-allylsulfanyl]-2-trifluoromethyl-phenoxy}-acetic acid ethyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 3,3-bis-(3-methyl-thiophen-2-yl)-prop-2-en-1-ol (110 mg, 0.44 mmol) and triphenylphosphine (220 mg, 0.88 mmol) in THF was added, at room temperature and under nitrogen atmosphere, DEAD (153 mg, 0.88 mmol). The reaction mixture was stirred for 5 min after which (2-trifluoromethyl-4-mercapto-phenoxy)-acetic acid ethyl ester (70 mg, 0.25 mmol) was added over 15 min. The reaction mixture was stirred at room temperature for 100 hours. The reaction mixture was evaporated and the crude residue was purified on a Horizon using a methylene chloride:heptanes gradient as eluent. The desired {4-[3,3-bis-(3-methyl-thiophen-2-yl)-allylsulfanyl]-2-trifluoromethyl-phenoxy}-acetic acid ethyl ester was isolated in 75 mg (59%) yield.

後処理

  1. additionwas added over 15 min
  2. customThe reaction mixture was evaporated
  3. customthe crude residue was purified on a Horizon

出典と根拠

ORDレコード
ord-a210a5d02894405799986db20db6f12d
出典データセット
uspto-grants-2006_10
特許番号
US07129268B2

反応ノート

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