1-Bromo-3,4-(methylenedioxy)benzene → 8-(Benzo[d][1,3]dioxol-5-yl)-1,4-dioxaspiro[4.5]decan-8-ol

HRID 273726

반응식

HRID 273726 반응식
[CH2:1]1[O:11][C:4]2([CH2:9][CH2:8][C:7](=[O:10])[CH2:6][CH2:5]2)[O:3][CH2:2]1.[Mg].Br[C:14]1[CH:22]=[CH:21][C:17]2[O:18][CH2:19][O:20][C:16]=2[CH:15]=1>C1COCC1>[O:18]1[C:17]2[CH:21]=[CH:22][C:14]([C:7]3([OH:10])[CH2:6][CH2:5][C:4]4([O:3][CH2:2][CH2:1][O:11]4)[CH2:9][CH2:8]3)=[CH:15][C:16]=2[O:20][CH2:19]1

참가 물질

5

반응물 3

HCID 758311-Bromo-3,4-(methylenedioxy)benzeneHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 5462224Magnesium

생성물 1

HCID 109128408-(Benzo[d][1,3]dioxol-5-yl)-1,4-dioxaspiro[4.5]decan-8-ol수율 85.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
25 °C

실험 절차

A solution of 1,4-cyclohexanedione monoethylene ketal (31.2 g, 0.2 mole) in 100 ml dry THF was added to a -60° C. solution of the Grignard reagent prepared from magnesium metal (7.2 g, 0.3 mole) and 5-bromo-1,3-benzodioxole (60.3 g, 0.3 mole). The mixture was allowed to warm to 25° C. and quenched with saturated NH4Cl and extracted with ether. The extracts were dried with Na2SO4 and the solvent removed in vacuo. The residue was crystallized from isopropyl ether to give the product (47.5 g, 85%, m.p: 103°-104° C.).

후처리

  1. customquenched with saturated NH4Cl
  2. extractionextracted with ether
  3. dry with materialThe extracts were dried with Na2SO4
  4. customthe solvent removed in vacuo
  5. customThe residue was crystallized from isopropyl ether

출처 및 근거

ORD 기록
ord-15c7f3e9bcc24627854a538a6ce836c5
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05387593

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