Dimethyl Sulfoxide → (4R)-5,5-Dimethyl-2-phenyl-1,3-dioxan-4-carbaldehyde

HRID 1671401노트

반응식

HRID 1671401 반응식
[CH3:1][C:2]1([CH3:16])[CH2:7][O:6][CH:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:4][C@H:3]1[CH2:14][OH:15].C(N(CC)CC)C.CS(C)=O>ClCCl>[CH3:1][C:2]1([CH3:16])[CH2:7][O:6][CH:5]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[O:4][C@H:3]1[CH:14]=[O:15]

참가 물질

5

반응물 3

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 67349301[(4R)-5,5-Dimethyl-2-phenyl-1,3-dioxan-4-yl]methan-1-ol

생성물 1

HCID 86628866(4R)-5,5-Dimethyl-2-phenyl-1,3-dioxan-4-carbaldehyde수율 75%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Following the general procedure for oxidation reactions of Description 7, 40.2 g (181.9 mmol) of [(4R)-5,5-dimethyl-2-phenyl-1,3-dioxan-4-yl]methan-1-ol (7a) in 1,100 mL of dichloromethane (DCM) in the presence of 126.8 mL (92.1 g, 0.910 mol) of triethylamine and 103.3 mL (113.8 g, 1.456 mol) of dimethylsulfoxide (DMSO) was reacted with 86.9 g (0.55 mol) of sulfur trioxide pyridine complex to afford 38.3 g (96% yield) of the crude title compound (7b). Purification by silica gel column chromatography using mixtures of methyl tert-butyl ether (MTBE) and hexane (Hxn) as eluent (MTBE/Hxn=1:9→MTBE/Hxn=1:6) provided 29.9 g (75% yield) of the title compound (7b) as a colorless liquid. Rf=0.58 (MTBE/Hxn=1:2). 1H NMR (400 MHz, CHCl3): δ=1.04 (s, 3H), 1.27 (s, 3H), 3.69 (d, J=11.6 Hz, 1H), 3.75 (d, J=11.2 Hz, 1H), 3.97 (d, J=1.2 Hz, 1H), 5.56 (s, 1H), 7.35-7.44 (m, 3H), 7.54-7.58 (m, 2H), 9.66 (d, J=1.6 Hz, 1H) ppm. MS (ESI) m/z: 221.0 (M+H)+, 242.9 (M+Na)+. The analytical data for the compound was consistent with that given in the literature (Ito et al., Synthesis, 1993, 137-140).

후처리

  1. customwas reacted with 86.9 g (0.55 mol) of sulfur trioxide pyridine complex
  2. customto afford 38.3 g (96% yield) of the crude title compound (7b)
  3. customPurification by silica gel column chromatography

출처 및 근거

ORD 기록
ord-d64d4a16599c4f199e003c04db39b963
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07994218B2

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