2-Hydroxyphenyltriphenylphosphonium bromide → Methyl E-4-{7-cyano-3-[2-(2-hydroxyphenyl)vinyl]heptyl}benzoate

HRID 1672682노트

반응식

HRID 1672682 반응식
[CH2:1]([Li])CCC.[Br-].[OH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[C:33]([CH2:35][CH2:36][CH2:37][CH2:38][CH:39]([CH:52]=O)[CH2:40][CH2:41][C:42]1[CH:51]=[CH:50][C:45]([C:46]([O:48][CH3:49])=[O:47])=[CH:44][CH:43]=1)#[N:34]>CCCCCC.C1COCC1>[C:33]([CH2:35][CH2:36][CH2:37][CH2:38][CH:39](/[CH:52]=[CH:1]/[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[OH:7])[CH2:40][CH2:41][C:42]1[CH:51]=[CH:50][C:45]([C:46]([O:48][CH3:49])=[O:47])=[CH:44][CH:43]=1)#[N:34]

참가 물질

6

반응물 3

HCID 573460052-Hydroxyphenyltriphenylphosphonium bromideHCID 57831357Methyl 4-(7-cyano-3-formylheptyl)benzoateHCID 178418339Butyllithium

생성물 1

HCID 57831335Methyl E-4-{7-cyano-3-[2-(2-hydroxyphenyl)vinyl]heptyl}benzoate수율 65%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

실험 절차

9.07 ml (14.52 mmol) of a 1.6 M solution of n-butyllithium in hexane are slowly added dropwise to a suspension of 3.26 g (7.26 mmol) of 2-hydroxyphenyltriphenylphosphonium bromide in 40 ml of dry THF at 0° C., and the mixture is stirred for 5 minutes. Then, at this temperature, 1.49 g (5.19 mmol) of methyl 4-(7-cyano-3-formylheptyl)benzoate from Example 94A in 10 ml of dry THF are slowly added dropwise. The reaction mixture is stirred at 0° C. for 10 minutes. The cooling is then removed, and the reaction solution is stirred at room temperature for 10 minutes and then mixed with silica gel and concentrated to dryness. The resulting residue is purified directly by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 1:2→1:5). 1.71 g (75% purity, 3.40 mmol, 65% yield) of an oil are obtained.

후처리

  1. stirringThe reaction mixture is stirred at 0° C. for 10 minutes
  2. customThe cooling is then removed
  3. stirringthe reaction solution is stirred at room temperature for 10 minutes
  4. additionmixed with silica gel
  5. concentrationconcentrated to dryness
  6. customThe resulting residue is purified directly by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 1:2→1:5)
  7. custom1.71 g (75% purity, 3.40 mmol, 65% yield) of an oil are obtained

출처 및 근거

ORD 기록
ord-971ab5ca0f214ef5870ac973b4dc4106
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07998988B2

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