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

HRID 274892

反応式

HRID 274892 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
25 °C

実験手順

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.).

後処理

  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

出典と根拠

ORDレコード
ord-17c43070656e40ccbb13ffb0c889c401
出典データセット
uspto-grants-1995_02
特許番号
US05391570

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