Water → 2-(3,5-Bis(trifluoromethyl)benzyloxymethyl)-2-phenyl-[1,3]dioxolane

HRID 548194ノート

反応式

HRID 548194 の反応式
[C:1]1([C:7]2([CH2:12][OH:13])[O:11][CH2:10][CH2:9][O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[F:16][C:17]([F:31])([F:30])[C:18]1[CH:19]=[C:20]([CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=1)[CH2:21]Br.O>CN(C=O)C>[F:16][C:17]([F:30])([F:31])[C:18]1[CH:19]=[C:20]([CH:23]=[C:24]([C:26]([F:29])([F:27])[F:28])[CH:25]=1)[CH2:21][O:13][CH2:12][C:7]1([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[O:11][CH2:10][CH2:9][O:8]1

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 1225733,5-Bis(trifluoromethyl)benzyl bromideHCID 126142482-Phenyl-1,3-dioxolane-2-methanol

生成物 1

HCID 866240352-(3,5-Bis(trifluoromethyl)benzyloxymethyl)-2-phenyl-[1,3]dioxolane収率 102%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

(2-Phenyl-[1,3]dioxolan-2-yl)methanol (14.82 g, 82 mmol) was dissolved in DMF (200 mL) and cooled with ice and sodium hydride (60% oily) (3.60 g, 90 mmol) was added thereto by dividing into two. The mixture was stirred for 1 hour under cooling with ice and for 2 hours at room temperature and then a solution of 3,5-bis(trifluoromethyl)benzyl bromide (16.5 mL, 90 mmol) in DMF (50 mL) was dropped thereinto during 30 minutes under cooling with ice. After the mixture was stirred for 2 hours under cooling with ice and for 20 hours at room temperature, the reaction mixture was added to water followed by extracting with ethyl acetate. The organic layers were combined, washed with a saturated saline solution and dried over anhydrous sodium sulfate. The residual oily product obtained by evaporation of the solvent in vacuo was purified by a silica gel column chromatography (n-hexane:ethyl acetate=19:1) to give 2-(3,5-bis(trifluoromethyl)benzyloxymethyl)-2-phenyl-[1,3]-dioxolane (34.00 g, 100%) as an oily product. 1H-NMR (DMSO-d6) δ: 3.67 (s, 2H), 3.79-3.84 (m, 2H), 4.02-4.08 (m, 2H), 4.74 (s, 2H), 7.31-7.39 (m, 3H), 7.46-7.49 (m, 2H), 7.89 (s, 2H), 7.96 (s, 1H).

後処理

  1. additionwas added
  2. temperatureduring 30 minutes under cooling with ice
  3. stirringAfter the mixture was stirred for 2 hours
  4. temperatureunder cooling with ice and for 20 hours at room temperature
  5. extractionby extracting with ethyl acetate
  6. washwashed with a saturated saline solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe residual oily product obtained by evaporation of the solvent in vacuo
  9. customwas purified by a silica gel column chromatography (n-hexane:ethyl acetate=19:1)

出典と根拠

ORDレコード
ord-bc2201bd43b548d189da05064ea8ea2c
出典データセット
uspto-grants-2011_05
特許番号
US07939552B2

反応ノート

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