Solketal → 2,2-Dimethyl-1,3-dioxolane-4-methanol 3,5-bistrifluoromethylbenzyl ether

HRID 55136

반응식

HRID 55136 반응식
[CH3:1][C:2]1([CH3:9])[O:6][CH:5]([CH2:7][OH:8])[CH2:4][O:3]1.[H-].[Na+].[F:12][C:13]([F:27])([F:26])[C:14]1[CH:15]=[C:16]([CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=1)[CH2:17]Br>CN(C=O)C.C1COCC1>[CH3:1][C:2]1([CH3:9])[O:6][CH:5]([CH2:7][OH:8])[CH2:4][O:3]1.[F:12][C:13]([F:27])([F:26])[C:14]1[CH:15]=[C:16]([CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=1)[CH2:17][O:8][CH2:7][C:5]1[CH:4]=[C:20]([C:22]([F:23])([F:24])[F:25])[CH:21]=[C:14]([C:13]([F:12])([F:26])[F:27])[CH:15]=1

참가 물질

5

반응물 3

HCID 7528SolketalHCID 24758Sodium hydrideHCID 1225733,5-Bis(trifluoromethyl)benzyl bromide

생성물 1

HCID 883788762,2-Dimethyl-1,3-dioxolane-4-methanol 3,5-bistrifluoromethylbenzyl ether

시약·촉매·용매 1

HCID 21974620tetrahydrofuran N,N-dimethylformamide용매

실험 절차

To a stirred solution of solketal (0.151 mol) in DMF/THF (1:1, 300 ml) under a nitrogen atmosphere was added sodium hydride (1.2 equivalents of an 80% dispersion in mineral oil). The anion was allowed to form over one hour prior to addition of 3,5-bistrifluoromethylbenzyl bromide. The reaction was partitioned between ethyl acetate-saturated ammonium chloride after 1 h and the organic phase separated, dried (MgSO4), and concentrated to a yellow oil. Chromatography using pet. ether then 20% ethyl acetate-pet. ether as eluent gave 2,2-dimethyl- 1,3-dioxolane-4-methanol-3,5-bistrifluoromethylbenzyl ether as a yellow oil: (CDCl3) δ1.4 (3H, s), 1.45 (3H, s), 3.6-3.65 (2H, m), 3.7-3.8 (1H, m), 4.1-4.15 (1H, m), 4.3-4.4 (1H, m), 4.7 (2H, s), 7.8 (3H, s).

후처리

  1. customto form over one hour
  2. customThe reaction was partitioned between ethyl acetate-saturated ammonium chloride after 1 h
  3. customthe organic phase separated
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated to a yellow oil

출처 및 근거

ORD 기록
ord-87d5ffb2faec404f88babb613a45a995
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05624947

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