Potassium Carbonate → Ethyl E-8-[2-(4-tert-butylbenzyloxy)phenyl]-6-(4-cyanobenzyl)oct-7-enoate

HRID 1672697노트

반응식

HRID 1672697 반응식
[C:1]([C:3]1[CH:28]=[CH:27][C:6]([CH2:7][CH:8](/[CH:18]=[CH:19]/[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[OH:26])[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:5][CH:4]=1)#[N:2].[C:29]([C:33]1[CH:40]=[CH:39][C:36]([CH2:37]Br)=[CH:35][CH:34]=1)([CH3:32])([CH3:31])[CH3:30].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:29]([C:33]1[CH:34]=[CH:35][C:36]([CH2:37][O:26][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2/[CH:19]=[CH:18]/[CH:8]([CH2:7][C:6]2[CH:27]=[CH:28][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:39][CH:40]=1)([CH3:32])([CH3:30])[CH3:31]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 878361-(Bromomethyl)-4-(1,1-dimethylethyl)benzeneHCID 57831344Ethyl E-6-(4-cyanobenzyl)-8-(2-hydroxyphenyl)oct-7-enoate

생성물 1

HCID 57831393Ethyl E-8-[2-(4-tert-butylbenzyloxy)phenyl]-6-(4-cyanobenzyl)oct-7-enoate수율 92.2%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A solution of 1.75 g (4.64 mmol) of ethyl E-6-(4-cyanobenzyl)-8-(2-hydroxyphenyl)oct-7-enoate from Example 112A in 50 ml of dry acetonitrile is mixed with 1579 mg (6.95 mmol) of 4-(tert-butyl)benzyl bromide and 961 mg (6.95 mmol) of anhydrous potassium carbonate and heated to reflux for 12 hours. The mixture is then concentrated to dryness. The residue is taken up in ethyl acetate, washed with water and saturated sodium chloride solution and dried over sodium sulfate. The organic phase is concentrated. The resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 8:1→4:1). 2.24 g (4.28 mmol, 92% yield) of a solid are obtained.

후처리

  1. temperatureheated
  2. temperatureto reflux for 12 hours
  3. concentrationThe mixture is then concentrated to dryness
  4. washwashed with water and saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. concentrationThe organic phase is concentrated
  7. customThe resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 8:1→4:1)

출처 및 근거

ORD 기록
ord-d2720c8034b741f2bbefd600b8732d93
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07998988B2

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