Chloromethyl Methyl Ether → HCID 88220868, 화합물

HRID 581021

반응식

HRID 581021 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][S:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:20][O:21][CH3:22].[Cl-].[Na+].O.[C:26]([O:29][CH2:30]C)(=O)C>CN(C)C=O>[CH3:20][O:21][CH2:22][O:16][C:13]1[CH:14]=[CH:15][C:10]([S:9][S:8][C:5]2[CH:4]=[CH:3][C:2]([O:1][CH2:26][O:29][CH3:30])=[CH:7][CH:6]=2)=[CH:11][CH:12]=1

참가 물질

6

반응물 4

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 2806654-[(4-Hydroxyphenyl)disulfanyl]phenolHCID 131718255Brine ethyl acetate

생성물 1

HCID 88220868HCID 88220868, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 4-hydroxyphenyldisulfide (650 mg, 2.60 mmol) in 10 mL of anhydrous N,N-dimethylformamide at 10° C. was added sodium hydride (230 mg, 5.75 mmol, 60% dispersion in mineral oil). After stirring for 15 minutes, chloromethylmethyl ether (0.44 mL, 5.75 mmol) was added via syringe. The reaction was warmed to ambient temperature and stirred for 0.5 hours. The mixture was distributed between brine/ethyl acetate (20 mL each). The layers were separated and the aqueous phase extracted with ethyl acetate (2×20 mL). The organic was dried (sodium sulfate) and concentrated to a yellow oil (993 mg, 100%). An analytical sample of 4-(methoxymethyloxy)-phenyldisulfide was prepared by chromatography (silicon dioxide, 4% ethyl acetate/hexanes). 1H NMR (DMSO-d6) d 7.40 (d, J=6.9 Hz, 4H), 7.00 (d, J=6.9 Hz, 4H), 5.15 (s, 4H), 3.32 (s, 6H). FD mass spec: 338. Anal. Calcd. for C16H18O4S2 : C, 56.78; H, 5.36. Found: C, 57.08; H, 5.44.

후처리

  1. stirringstirred for 0.5 hours
  2. customThe layers were separated
  3. extractionthe aqueous phase extracted with ethyl acetate (2×20 mL)
  4. dry with materialThe organic was dried (sodium sulfate)
  5. concentrationconcentrated to a yellow oil (993 mg, 100%)

출처 및 근거

ORD 기록
ord-adcca7a3ec7e4e9d9b0cea250ce2a757
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05919800

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