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

HRID 1172825

반응식

HRID 1172825 반응식
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]

참가 물질

8

반응물 6

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-40 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8ab7dbe4dfac470a9b7aa4d9fdbe6be1
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834036B2

연결된 노트

불러오는 중…