Sodium Carbonate → 2-Methyl-2-cyano-7-(2-ethyl-4-(4-fluorophenyl)-5-benzyloxyphenoxy)heptane

HRID 2211373노트

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HRID 2211373 반응식
[CH3:1][C:2]([C:27]#[N:28])([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:13](Br)=[CH:12][C:11]=1[CH2:25][CH3:26])[CH3:3].C(=O)([O-])[O-].[Na+].[Na+].[F:35][C:36]1[CH:41]=[CH:40][C:39](B(O)O)=[CH:38][CH:37]=1>C1C=CC=CC=1.C(O)C.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][C:2]([C:27]#[N:28])([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:13]([C:39]2[CH:40]=[CH:41][C:36]([F:35])=[CH:37][CH:38]=2)=[CH:12][C:11]=1[CH2:25][CH3:26])[CH3:3]

참가 물질

8

반응물 3

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 106709472-Methyl-2-cyano-7-(2-ethyl-4-bromo-5-benzyloxyphenoxy)heptane

생성물 1

HCID 117981752-Methyl-2-cyano-7-(2-ethyl-4-(4-fluorophenyl)-5-benzyloxyphenoxy)heptane수율 93%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 241Benzene용매HCID 702Ethanol용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 1.5 g of 2-methyl-2-cyano-7-(2-ethyl-4-bromo-5-benzyloxyphenoxy)heptane and 0.5 g of tetrakis(triphenylphosphine)palladium(0) in 70 mL of benzene was stirred with 15 mL of 2.0M sodium carbonate. A solution of 1.1 g of 4-fluorophenyl boronic acid in 15 mL of ethanol was added. The mixture was heated at reflux for 16 hours. The mixture was cooled and diluted with ethyl acetate. The organic phase was washed with saturated ammonium chloride, washed with saturated sodium chloride, dried over sodium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel eluting with hexane/ethyl ether to provide 1.44 g (93%) of the desired title intermediate. NMR.

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 16 hours
  3. temperatureThe mixture was cooled
  4. washThe organic phase was washed with saturated ammonium chloride
  5. washwashed with saturated sodium chloride
  6. dry with materialdried over sodium sulfate
  7. customevaporated in vacuo
  8. customThe residue was chromatographed on silica gel eluting with hexane/ethyl ether

출처 및 근거

ORD 기록
ord-852602f348f54ad4b94b8e9104cdd313
출처 데이터셋
uspto-grants-1995_10
특허 번호
US05462954

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