Phenacyl bromide → 2-[2,5-Bis(benzyloxy)phenoxy]-1-phenylethanone

HRID 31214ノート

反応式

HRID 31214 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][C:10]=1[OH:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:25][C:26]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:27].C(=O)([O-])O.[K+].C1OCCOCCOCCOCCOCCOC1>C(#N)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][C:10]=1[O:23][CH2:25][C:26]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:27])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 6259Phenacyl bromideHCID 2855718-Crown-6HCID 516893Potassium BicarbonateHCID 155069722,5-Bis(benzyloxy)phenol

生成物 1

HCID 179784822-[2,5-Bis(benzyloxy)phenoxy]-1-phenylethanone

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
22 °C

実験手順

A mixture of 2,5-bis(benzyloxy)phenol (0.28 g), 2-bromoacetophenone (0.22 g), potassium hydrogen-carbonate (0.25 g) and 18-Crown-6 (3 mg) in acetonitrile (4.2 ml) was stirred at 22° C. for one week. The mixture was filtered and evaporated to dryness under reduced pressure. The residue was triturated with the mixture of ether (8.2 ml) and water (1.4 ml) at the ice bath temperature. The product was collected by filtration, washed with cold ether and dried under reduced pressure. Yield is 0.14 g. 1H NMR (DMSO-d6) δ=4.98 (s, 2H), 5.06 (s, 2H), 5.58 (s, 2H), 6.51 (dd, J=8.9, 2.3 Hz, 1H), 6.68 (d, J=2.3 Hz, 1H), 6.94 (d, J=8.9 Hz, 1H), 7.28-8.03 (m, 15H).

後処理

  1. filtrationThe mixture was filtered
  2. customevaporated to dryness under reduced pressure
  3. customThe residue was triturated with the mixture of ether (8.2 ml) and water (1.4 ml) at the ice bath temperature
  4. filtrationThe product was collected by filtration
  5. washwashed with cold ether
  6. customdried under reduced pressure

出典と根拠

ORDレコード
ord-7f9a6aad03f3423b9c5a65a32fd0e897
出典データセット
uspto-grants-2008_09
特許番号
US07425568B2

反応ノート

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