Water → 2-(1-methoxy-2-methyl-2,3-dihydro-1H-inden-4-yl)ethanol

HRID 1047466ノート

反応式

HRID 1047466 の反応式
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH:5]([CH3:13])[CH:6]2[O:11][CH3:12].[Li]CCCC.[CH2:19]1[O:21][CH2:20]1.O>C1COCC1>[CH3:12][O:11][CH:6]1[C:7]2[C:3](=[C:2]([CH2:19][CH2:20][OH:21])[CH:10]=[CH:9][CH:8]=2)[CH2:4][CH:5]1[CH3:13]

参加物

6

反応物 4

HCID 962WaterHCID 6354Ethylene OxideHCID 64228144-Bromo-2-methyl-1-(methyloxy)-2,3-dihydro-1H-indeneHCID 178418339Butyllithium

生成物 1

HCID 584187692-(1-methoxy-2-methyl-2,3-dihydro-1H-inden-4-yl)ethanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-110 °C

実験手順

To a solution of 20.0 g (82.9 mmol) of 4-bromo-2-methyl-methoxyindane in 200 ml of THF 33.2 ml of 2.5 M (83.0 mmol) n-BuLi in hexanes was added for 20 min at −80° C. This mixture was stirred for 40 min at this temperature, cooled to −110° C., and 4.38 g (99.4 mmol) of ethylene oxide was added by one portion at vigorous stirring. The resulting mixture was stirred for 12 h at room temperature, and then 10 ml of water was added. The organic layer was separated and evaporated to dryness. To the residue 200 ml of water was added, and the crude product was extracted with 3×100 ml of dichloromethane. The combined organic extract was dried over Na2SO4 and evaporated to dryness. The product was isolated by flash chromatography using short column with Silica Gel 60 (40-63 um, d 110 mm, 190 mm; eluent: hexanes/ether=20/1). Yield 12.7 g (74%) of a ca. 1 to 1.2 mixture of two diastereomers.

後処理

  1. stirringThe resulting mixture was stirred for 12 h at room temperature
  2. customThe organic layer was separated
  3. customevaporated to dryness
  4. additionTo the residue 200 ml of water was added
  5. extractionthe crude product was extracted with 3×100 ml of dichloromethane
  6. extractionThe combined organic extract
  7. dry with materialwas dried over Na2SO4
  8. customevaporated to dryness
  9. customThe product was isolated by flash chromatography
  10. additionYield 12.7 g (74%) of a ca. 1 to 1.2 mixture of two diastereomers

出典と根拠

ORDレコード
ord-4752fe46a52443be9a78d3a625278808
出典データセット
uspto-grants-2013_10
特許番号
US08569532B2

反応ノート

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