Pyridine → Toluene-4-sulfonic acid 4-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexylmethyl ester

HRID 16056

반응식

HRID 16056 반응식
[C:1]([SiH2:5][O:6][C:7]([CH3:17])([CH3:16])[CH:8]1[CH2:13][CH2:12][CH:11]([CH2:14][OH:15])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[S:18](Cl)([C:21]1[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=1)(=[O:20])=[O:19].N1C=CC=CC=1.CCOCC>C(Cl)(Cl)Cl>[C:1]([SiH2:5][O:6][C:7]([CH3:17])([CH3:16])[CH:8]1[CH2:9][CH2:10][CH:11]([CH2:14][O:15][S:18]([C:21]2[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=2)(=[O:20])=[O:19])[CH2:12][CH2:13]1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 4

HCID 1049PyridineHCID 3283Diethyl EtherHCID 73974-Toluenesulfonyl chlorideHCID 131725186HCID 131725186, 화합물

생성물 1

HCID 131726432Toluene-4-sulfonic acid 4-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexylmethyl ester수율 83%

시약·촉매·용매 1

HCID 6212Chloroform용매

반응 조건

온도
25 °C

실험 절차

To a 100 mL-flask containing 83 (3.4 g, 13.2 mmol) in CHCl3 (30 mL) was added tosyl chloride (3.26 g, 17.1 mmol) and pyridine (3.2 mL, 39.6 mmol). The reaction was allowed to stir at 25° C. for 14 hours after which time the reaction was concentrated in vacuo to yield a wet white solid. To this solid was added ether (50 mL) and the solid was filtered and subsequently washed with additional ether (2×50 mL). The ether layers were pooled, concentrated in vacuo to yield a clear oil which was purified by flash chromatography, on a silica gel column, eluting with 1:4 ether/petroleum ether to yield 84 (4.5 g, 83%) as a white solid. 1H NMR (CDCl3) δ 7.78 (d, J=7.7, 2 H), 7.33 (d, J=7.7 Hz, 2 H), 3.81 (d, J=6.2 Hz, 2H), 3.37 (d, J=6.2, 2 H), 2.44 (s, 3 H), 1.95-1.72 (m, 4 H), 1.65 (m, 1 H), 1.40 (m, 1 H), 1.03-0.89 (m, 4 H), 0.88 (s, 9 H), 0.04 (s, 6 H); 13C NMR (CDCl3) δ 145.1, 133.7, 130.3, 128.4, 75.8, 68.9, 40.7, 38.0, 29.1, 26.5, 22.1, 18.9, −4.9; APCI m/z (rel intensity) 413 (MH+, 100).

후처리

  1. concentrationwas concentrated in vacuo
  2. customto yield a wet white solid
  3. filtrationthe solid was filtered
  4. washsubsequently washed with additional ether (2×50 mL)
  5. concentrationconcentrated in vacuo
  6. customto yield a clear oil which
  7. customwas purified by flash chromatography, on a silica gel column
  8. washeluting with 1:4 ether/petroleum ether

출처 및 근거

ORD 기록
ord-2b8d2960e6dd41e7909556bcefdecec1
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737127B2

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