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

HRID 548194노트

반응식

HRID 548194 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

(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).

후처리

  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)

출처 및 근거

ORD 기록
ord-bc2201bd43b548d189da05064ea8ea2c
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07939552B2

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