Triphenylphosphine → 3-[(Tert-butyldimethylsilyloxy)methyl]-6-[(2-trifluoromethylphenyloxy)methyl]-1,2-dithiin

HRID 265312

반응식

HRID 265312 반응식
[OH:1][CH2:2][C:3]1[S:4][S:5][C:6]([CH2:9][O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])=[CH:7][CH:8]=1.[F:18][C:19]([F:28])([F:27])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1.C(OCC)(=O)C.CCCCCC>[Si:11]([O:10][CH2:9][C:6]1[S:5][S:4][C:3]([CH2:2][O:1][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[C:19]([F:28])([F:27])[F:18])=[CH:8][CH:7]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:12])[CH3:13]

참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 679582-TrifluoromethylphenolHCID 5462977Diethyl azodicarboxylateHCID 100628323-[(Tert-butyldimethylsilyloxy)methyl]-6-hydroxymethyl-1,2-dithiin

생성물 1

HCID 117436603-[(Tert-butyldimethylsilyloxy)methyl]-6-[(2-trifluoromethylphenyloxy)methyl]-1,2-dithiin수율 37%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 21226206Ethyl acetate hexane용매

반응 조건

온도
0 °C

실험 절차

To a stirred solution of 3-(hydroxymethyl)-6-[(tert-butyldimethylsilyloxy)methyl]-1,2-dithiin (U.S. Ser. No. 08/212,096) (200 mg, 0.69 mmol) in 5 mL dry THF was added a solution of 2-(trifluoromethyl)phenol (223 mg, 1.37 mmol) in 5 mL THF, followed by addition of triphenylphosphine (234 mg, 0.89 mmol) The resulting solution was cooled to 0° C., then 140 μL (156 mg, 0.89 mmol) of diethylazodicarboxylate was added, and the reaction mixture was kept at 0°-5° C. until TLC analysis showed the reaction to be complete. For isolation of the products, the reaction mixture poured directly onto a silica gel column using ethyl acetate-hexane, 1:3, to provide 110 mg (37%) of 3-[(tert-butyldimethylsilyloxy)methyl]-6-[(2-trifluoromethylphenyloxy)methyl]-1,2-dithiin; 1H NMR (CDCl3):δ7.56 (d, J=8.0, 1 H), 7.45 (t, J=8.0, 1 H), 7.01 (m, 2 H), 6.49 S (d, J=6.0 Hz, 1 H), 6.37 (d, J=6.0 Hz, 1 H), 4.71 (s, 2 H), 4.26 (s, 2 H), 0.88 (s, 9 H), 0.07 (s, 6 H); 13C NMR (CDCl3):δquaternary carbons missing, 136.19, 133.24, 127.23, 123.57, 120.81, 113.15, 69.58, 64.85, 25.79, 18.34, -5.38; MS (LSIMS) (M+) 434.1.

후처리

  1. customwas kept at 0°-5° C. until TLC analysis
  2. customthe reaction
  3. additionFor isolation of the products, the reaction mixture poured directly onto a silica gel column

출처 및 근거

ORD 기록
ord-44afbc84d7524090b51e854915598088
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05648354

연결된 노트

불러오는 중…