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

HRID 1455019노트

반응식

HRID 1455019 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
22 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-9a9ebfe5a18447e0a969a4933d2baec9
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07482340B2

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