Tributylphosphine → HCID 23082820、化合物

HRID 2422284ノート

反応式

HRID 2422284 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[CH3:14][C:15]1[CH:16]=[C:17]([CH:27]=[CH:28][CH:29]=1)[O:18][C:19]1[CH:20]=[C:21]([CH2:25]O)[CH:22]=[CH:23][CH:24]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1(C)C=CC=CC=1.CCCCCC>[CH3:25][C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][CH:22]=1)[O:18][C:17]1[CH:16]=[C:15]([CH:29]=[CH:28][CH:27]=1)[CH2:14][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:7]=1

参加物

7

反応物 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 79706Benzenepropanoic acid, 4-hydroxy-, methyl esterHCID 23083121[3-(3-Methylphenoxy)phenyl]methanol

生成物 1

HCID 23082820HCID 23082820、化合物収率 55%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8058Hexane溶媒

実験手順

A solution of methyl 3-(4-hydroxyphenyl)propanoate (0.396 g, 2.20 mmol), [3-(3-methylphenoxy)phenyl]methanol (0.429 g, 2.00 mmol) and tributylphosphine (0.747 mL, 3.00 mmol) in toluene (30 mL) was stirred under ice-cooling, 1,1′-(azodicarbonyl)dipiperidine (0.757 g, 3.00 mmol) was added by small portions, the temperature was raised to room temperature and the mixture was stirred for 18 hrs. Hexane (15 mL) was added to the reaction mixture, the precipitated insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane-20% ethyl acetate/hexane) and preparative HPLC (10-95% acetonitrile/water, containing 0.1% trifluoroacetic acid) to give the title compound (0.414 g, yield 55%) as a pale-yellow oil.

後処理

  1. temperaturecooling
  2. filtrationthe precipitated insoluble material was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel chromatography (hexane-20% ethyl acetate/hexane) and preparative HPLC (10-95% acetonitrile/water, containing 0.1% trifluoroacetic acid)

出典と根拠

ORDレコード
ord-d3d33c8b22534448abd0b87696b05cac
出典データセット
uspto-grants-2011_06
特許番号
US07960369B2

反応ノート

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