Hexane → [4-Chloro-2-fluoro-5-methoxy-3-(trimethylsilyl)phenyl][4-(4-chlorophenoxy)-2-propylphenyl]methanol

HRID 1172825

反応式

HRID 1172825 の反応式
CC1(C)CCCC(C)(C)N1.C([Li])CCC.CCCCCC.[F:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([Cl:31])[C:24]=1[Si:32]([CH3:35])([CH3:34])[CH3:33].[Cl:36][C:37]1[CH:54]=[CH:53][C:40]([O:41][C:42]2[CH:49]=[CH:48][C:45]([CH:46]=[O:47])=[C:44]([CH2:50][CH2:51][CH3:52])[CH:43]=2)=[CH:39][CH:38]=1.[Cl-].[NH4+]>C1COCC1>[Cl:31][C:25]1[C:26]([O:29][CH3:30])=[CH:27][C:28]([CH:46]([C:45]2[CH:48]=[CH:49][C:42]([O:41][C:40]3[CH:53]=[CH:54][C:37]([Cl:36])=[CH:38][CH:39]=3)=[CH:43][C:44]=2[CH2:50][CH2:51][CH3:52])[OH:47])=[C:23]([F:22])[C:24]=1[Si:32]([CH3:34])([CH3:33])[CH3:35]

参加物

8

反応物 6

HCID 8058HexaneHCID 130352,2,6,6-TetramethylpiperidineHCID 25517Ammonium ChlorideHCID 46941339(2-Chloro-6-fluoro-3-methoxyphenyl)trimethylsilaneHCID 574201434-(4-Chlorophenoxy)-2-propylbenzaldehydeHCID 178418339Butyllithium

生成物 1

HCID 86622409[4-Chloro-2-fluoro-5-methoxy-3-(trimethylsilyl)phenyl][4-(4-chlorophenoxy)-2-propylphenyl]methanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-40 °C

実験手順

To a solution of 2,2,6,6-tetramethylpiperidine (2.75 g, 10 mmol) in THF (50 mL) cooled at −75° C. was added a solution of n-butyllithium in hexane (1.6 M, 6.3 mL, 10 mmol). After 15 min, 4-fluoro-2-chloro-3-(trimethylsilyl)anisole (2.3 g, 10 mmol) was added and the solution was warmed gradually to −40° C. over a 2 h period. The solution was recooled to −75° C. and a solution of the aldehyde from Step 1 of Example 3 (1.4 g, 5.0 mmol) in THF (3 mL) was added quickly. The reaction mixture was stirred for 15 min., poured into a saturated aqueous solution of ammonium chloride and extracted with ethyl acetate. After removal of the solvent, the residue was purified by chromatography on silica gel to give the title product.

後処理

  1. customwas recooled to −75° C.
  2. extractionextracted with ethyl acetate
  3. customAfter removal of the solvent
  4. customthe residue was purified by chromatography on silica gel

出典と根拠

ORDレコード
ord-8ab7dbe4dfac470a9b7aa4d9fdbe6be1
出典データセット
uspto-grants-2010_11
特許番号
US07834036B2

関連ノート

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