Triphenylphosphine → [2-(4-Pyrazole-1-yl-phenoxy)-ethyl]-carbamic acid benzyl ester

HRID 49397

反応式

HRID 49397 の反応式
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:33][CH2:34][NH:35][C:36](=[O:45])[O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1.C1(C)C=CC=CC=1>[CH2:38]([O:37][C:36](=[O:45])[NH:35][CH2:34][CH2:33][O:12][C:9]1[CH:10]=[CH:11][C:6]([N:1]2[CH:5]=[CH:4][CH:3]=[N:2]2)=[CH:7][CH:8]=1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

参加物

7

反応物 4

HCID 11776TriphenylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 280458benzyl N-(2-hydroxyethyl)carbamateHCID 124631314-(1H-Pyrazol-1-yl)phenol

生成物 1

HCID 69743538[2-(4-Pyrazole-1-yl-phenoxy)-ethyl]-carbamic acid benzyl ester

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒2 回HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A round-bottomed flask was charged with 4-pyrazole-1-yl-phenol (175 mg, 1.09 mmol), and 3.6 ml of toluene, triphenylphosphine (430 mg, 1.64 mmol), and benzyl N-(2-hydroxyethyl)carbamate (320 mg, 1.64 mmol) were then added. The solution was cooled to 0° C. and 1,1′-(azodicarbonyl)-dipiperidine (414 mg, 1.64 mmol) was added. The mixture was allowed to stir for about ten minutes at about 0° C. and was then allowed to warm to room temperature. An additional 3.6 ml of toluene and 3.6 ml of tetrahydrofuran were added to the viscous solution. The reaction mixture was stirred for about forty-eight hours, and the precipitated solids were filtered off and washed with a minimum volume of 1:1 toluene/tetrahydrofuran. The filtrate was concentrated in vacuo to afford the intermediate [2-(4-pyrazole-1-yl-phenoxy)-ethyl]-carbamic acid benzyl ester as an oil which was used directly in the next step.

後処理

  1. additionwere then added
  2. temperatureto warm to room temperature
  3. stirringThe reaction mixture was stirred for about forty-eight hours
  4. filtrationthe precipitated solids were filtered off
  5. washwashed with a minimum volume of 1:1 toluene/tetrahydrofuran
  6. concentrationThe filtrate was concentrated in vacuo

出典と根拠

ORDレコード
ord-f0b76ac4a464470591643685e1918438
出典データセット
uspto-grants-2004_03
特許番号
US06706743B2

関連ノート

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