Dimethyl Sulfoxide → HCID 59835994, 화합물

HRID 271994노트

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HRID 271994 반응식
[CH3:1][C:2]([CH3:21])([CH3:20])[C:3]([N:5]1[CH2:10][CH2:9][C:8]([CH2:17][CH2:18][OH:19])([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:7][CH2:6]1)=[O:4].CS(C)=O.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH3:1][C:2]([CH3:21])([CH3:20])[C:3]([N:5]1[CH2:10][CH2:9][C:8]([CH2:17][CH:18]=[O:19])([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:7][CH2:6]1)=[O:4]

참가 물질

5

반응물 3

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 689336852-[3-(2,2-Dimethylpropanoyl)-6-phenyl-1,3-oxazinan-6-yl]ethanol

생성물 1

HCID 59835994HCID 59835994, 화합물수율 98%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

To a 0° C. solution of the above 2-[3-(2,2-dimethylpropanoyl)-6-phenyl-1,3-oxazinan-6-yl]ethanol, dimethyl sulfoxide (10 mL, 141 mmol) and diisopropylethylamine (10.5 mL, 60 mmol) in 60 mL CH2Cl2 was added SO3.pyr (9.0 g, 57 mmol) in one portion. The reaction mixture was stirred at 0° C. for 2 h, quenched with saturated aqueous NaHCO3, extracted with CHCl3, dried (Na2SO4) and chromatographed (2:1 Hex:EtOAc) to provide [3-(2,2-dimethylpropanoyl)-6-phenyl-1,3-oxazinan-6-yl]acetaldehyde (2.84 g, 98%) as an oil. 1H NMR (400 MHz, CDCl3): δ 9.64 (t, 1H, J=2.7 Hz), 7.45-7.41 (m, 4H), 7.33 (m, 1H), 5.49 (dd, 1H, J=11.1, 1.9 Hz), 4.74 (d, 1H, J=11.5 Hz), 4.27 (m, 1H), 3.08 (m, 1H), 2.72 (ABqd, 2H, J=15.3, 2.8 Hz), 2.43 (ddd, 1H, J=14.2, 4.1, 3.0 Hz), 2.11 (ddd, 1H, J=14.2; 11.4, 4.3 Hz), 1.28 (s, 9H). ESI-MS 312 (M+Na).

후처리

  1. customquenched with saturated aqueous NaHCO3
  2. extractionextracted with CHCl3
  3. dry with materialdried (Na2SO4)
  4. customchromatographed (2:1 Hex:EtOAc)

출처 및 근거

ORD 기록
ord-aba813ce88c240f098975c565aa426d4
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07452992B2

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