Ethyl bromoacetate → (4-Benzyloxy-naphthalen-1-yloxy)-acetic Acid Ethyl Ester

HRID 1727001ノート

反応式

HRID 1727001 の反応式
[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([OH:19])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH2:25]([O:24][C:22](=[O:23])[CH2:21][O:19][C:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:10][CH:11]=1)[CH3:26]

参加物

5

反応物 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 5629374-(Benzyloxy)naphthalen-1-ol

生成物 1

HCID 69035941(4-Benzyloxy-naphthalen-1-yloxy)-acetic Acid Ethyl Ester収率 82.9%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A mixture of 2 g (8 mmol) of 4-benzyloxy-naphthalen-1-ol [Journal of Medicinal Chemistry (1985), 28(6), 822-41, of 2.67 g (16 mmol) of ethyl bromoacetate and of 3.12 g (9.6 mmol) of cesium carbonate in 30 ml of acetonitrile was stirred at 60° C. for 3 hours. Subsequently, the reaction mixture was evaporated to dryness and the residue was partitioned between water and tert.-butyl methyl ether. The organic phase was separated, washed with water and brine, dried over anhydrous sodium sulfate and finally evaporated. 2.23 g of the title compound were obtained as white crystals after crystallization from n-heptane.

後処理

  1. customSubsequently, the reaction mixture was evaporated to dryness
  2. customthe residue was partitioned between water and tert.-butyl methyl ether
  3. customThe organic phase was separated
  4. washwashed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customfinally evaporated

出典と根拠

ORDレコード
ord-f1b7579b99f045dba5a12f5cdc5fbb40
出典データセット
uspto-grants-2009_02
特許番号
US07495001B2

反応ノート

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