Hydrochloric Acid → 2-(3-Bromobenzyl)-1,3-propanediol

HRID 857212ノート

反応式

HRID 857212 の反応式
C1(C)C=CC=CC=1.[H-].[Br:9][C:10]1[CH:11]=[C:12]([CH:25]=[CH:26][CH:27]=1)[CH2:13][CH:14]([C:20](OCC)=[O:21])[C:15](OCC)=[O:16].Cl>CO>[Br:9][C:10]1[CH:11]=[C:12]([CH:25]=[CH:26][CH:27]=1)[CH2:13][CH:14]([CH2:15][OH:16])[CH2:20][OH:21]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 11056569Diethyl (3-bromobenzyl)malonateHCID 86595848Hydride toluene

生成物 1

HCID 218669482-(3-Bromobenzyl)-1,3-propanediol収率 48.7%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To an ice-cooled 94 ml of 1.0 M diisobutylalminium hydride toluene solution was added dropwise 5.41 g of diethyl (3-bromobenzyl)malonate at 15° C. or less under argon flow. The mixture was stirred for 30 minutes under ice-cooling, warmed to room temperature and stirred for 2 hours. The reaction solution was ice-cooled, and 21 ml of methanol was added dropwise slowly, then 41 ml of 2 N hydrochloric acid was added dropwise. The mixture was stirred for 20 minutes at room temperature. The reaction solution was filtered to remove insolubles, extracted with ethyl acetate, washed with saturated sodium hydrogen carbonate, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (Wakogel® C-200, chloroform: methanol=10:1) to provide 1.96 g of the objective compound as white crystals. M.p. 61-63° C.

後処理

  1. temperaturecooling
  2. stirringstirred for 2 hours
  3. temperaturecooled
  4. stirringThe mixture was stirred for 20 minutes at room temperature
  5. filtrationThe reaction solution was filtered
  6. customto remove insolubles
  7. extractionextracted with ethyl acetate
  8. washwashed with saturated sodium hydrogen carbonate
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated
  11. customThe residue was purified by silica gel column chromatography (Wakogel® C-200, chloroform: methanol=10:1)

出典と根拠

ORDレコード
ord-b057ceb4ef7f4f249eed97f2dea138a0
出典データセット
uspto-grants-2006_12
特許番号
US07144906B2

反応ノート

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