Ethylene carbonate → 2-(1,3-Benzoxazol-4-yloxy)ethanol

HRID 493310

反応式

HRID 493310 の反応式
C([O-])([O-])=O.[K+].[K+].[OH:7][C:8]1[C:13]2[N:14]=[CH:15][O:16][C:12]=2[CH:11]=[CH:10][CH:9]=1.C1(=O)O[CH2:20][CH2:19][O:18]1>CN(C=O)C.O.CO>[O:16]1[C:12]2[CH:11]=[CH:10][CH:9]=[C:8]([O:7][CH2:20][CH2:19][OH:18])[C:13]=2[N:14]=[CH:15]1

参加物

7

反応物 3

HCID 7303Ethylene carbonateHCID 11430Potassium CarbonateHCID 137206971,3-Benzoxazol-4-ol

生成物 1

HCID 220363922-(1,3-Benzoxazol-4-yloxy)ethanol

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

K2CO3 (254 mg, 1.84 mmol) was added to a stirred solution of 4-hydroxybenzoxazole* (248 mg, 1.84 mmol) in DMF (5 mL) at room temperature. The mixture was heated at 90° C. for 15 min and ethylene carbonate (176 mg, 2.00 mmol) was added. The mixture was stirred at 150° C. for 2 h and allowed to attain room temperature. The mixture was diluted with water (2 mL) and MeOH (2 mL), and concentrated. The residue was partitioned between water and CH2Cl2. The aqueous layer was separated and extracted with CH2Cl2 (2×10 mL). The organic phases were pooled and washed with water and brine, and dried over MgSO4. The filtrate was concentrated to give the product as a brown oil that slowly solidified: yield 278 mg (84%), mp 47-49° C. Anal (C9H9NO3) C, H, N.

後処理

  1. customto attain room temperature
  2. concentrationconcentrated
  3. customThe residue was partitioned between water and CH2Cl2
  4. customThe aqueous layer was separated
  5. extractionextracted with CH2Cl2 (2×10 mL)
  6. washwashed with water and brine
  7. dry with materialdried over MgSO4
  8. concentrationThe filtrate was concentrated

出典と根拠

ORDレコード
ord-cc74601e8b4f4fbdbb8e56bcc197d43c
出典データセット
uspto-grants-2009_05
特許番号
US07534794B2

関連ノート

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