Ammonium Chloride → 1-(1,3-Dioxolan-2-yl)-1,4-epoxy-1,4-dihydronaphthalene

HRID 1165463

反応式

HRID 1165463 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1F.[O:9]1[CH2:13][CH2:12][O:11][CH:10]1[C:14]1[O:15][CH:16]=[CH:17][CH:18]=1.[Mg].[NH4+].[Cl-]>C1COCC1>[O:9]1[CH2:13][CH2:12][O:11][CH:10]1[C:14]12[O:15][CH:16]([C:2]3[C:7]1=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:17]=[CH:18]2

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 612591-Bromo-2-fluorobenzeneHCID 2631582-Furyl-1,3-dioxolaneHCID 5462224Magnesium

生成物 1

HCID 142086951-(1,3-Dioxolan-2-yl)-1,4-epoxy-1,4-dihydronaphthalene収率 77.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

2-Bromofluorobenzene (36.0 g, 0.222M) in THF (200 ml) was added dropwise over one hour to a refluxing mixture of the above furan (28.0 g, 0.200M) and magnesium turnings (5.4 g, 0.206M) in dry THF (200 ml) under nitrogen. After the addition was complete, refluxing was continued for one hour. The cooled mixture was then poured onto saturated NH4Cl solution (250 ml), the organic layer separated and the aqueous layer re-extracted with ether. The combined organic extract was washed with saturated NH4Cl solution, dried over anhydrous K2CO3 --Na2SO4 and concentrated in vacuo. The residue was purified on the Waters Prep 500 HPLC using two columns and eluting with EtOAc/hexane (1:4). A total of 33.3 g of 1-(1,3-dioxolan-2-yl)-1,4-epoxy-1,4-dihydronaphthalene was obtained as a pale yellow oil. Crystallization of the oil from hexane gave 32.5 g (75% yield) as white crystals, mp 48°-49° C.

後処理

  1. additionAfter the addition
  2. temperaturerefluxing
  3. customthe organic layer separated
  4. extractionthe aqueous layer re-extracted with ether
  5. extractionThe combined organic extract
  6. washwas washed with saturated NH4Cl solution
  7. dry with materialdried over anhydrous K2CO3
  8. concentrationNa2SO4 and concentrated in vacuo
  9. customThe residue was purified on the Waters Prep 500 HPLC
  10. washeluting with EtOAc/hexane (1:4)

出典と根拠

ORDレコード
ord-bd346781965d42fea03fce4e58433439
出典データセット
uspto-grants-1990_03
特許番号
US04910198

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