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Acetic Anhydride → trans-2-[3-(2-Oxopropylsulfonyl)-4-n-propoxy-5-benzyloxyphenyl]-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran

HRID 1196696
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Reaktionsgleichung

Reaktionsgleichung von HRID 1196696
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([C@H:23]2[CH2:27][CH2:26][C@H:25]([C:28]3[CH:33]=[C:32]([O:34][CH3:35])[C:31]([O:36][CH3:37])=[C:30]([O:38][CH3:39])[CH:29]=3)[O:24]2)[CH:8]=[C:9]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:10]=1[O:11][CH2:12][CH2:13][CH3:14])(=[O:4])=[O:3].[Li]CCCC.[C:45](OC(=O)C)(=[O:47])[CH3:46].[Cl-].[NH4+]>C1COCC1.CCOCC.O>[O:47]=[C:45]([CH3:46])[CH2:1][S:2]([C:5]1[CH:6]=[C:7]([C@H:23]2[CH2:27][CH2:26][C@H:25]([C:28]3[CH:33]=[C:32]([O:34][CH3:35])[C:31]([O:36][CH3:37])=[C:30]([O:38][CH3:39])[CH:29]=3)[O:24]2)[CH:8]=[C:9]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:10]=1[O:11][CH2:12][CH2:13][CH3:14])(=[O:4])=[O:3]
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Komponenten

8

Edukt 4

HCID 7918Acetic AnhydrideHCID 25517Ammonium ChlorideHCID 15078288racemic trans-2-(3-Methylsulfonyl-4-n-propoxy-5-benzyloxyphenyl)-5-(3,4,5-trimethoxyphenyl) tetrahydrofuranHCID 178418339Butyllithium

Produkt 1

HCID 15078289trans-2-[3-(2-Oxopropylsulfonyl)-4-n-propoxy-5-benzyloxyphenyl]-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2.7 g trans-2-(3-methylsulfonyl-4-n-propoxy-5-benzyloxyphenyl)-5-(3,4,5-trimethoxyphenyl) tetrahydrofuran (STEP I) dissolved in 15 mL THF was cooled to -78° and treated with 5.3 mL of 1.6M n-BuLi. After about 5 minutes of stirring, to the resulting dark solution, 1.0 mL of acetic anhydride was added. The yellow reaction mixture was allowed to warm up to room temperature and treated with 3-4 g of solid ammonium chloride, water and ether. NMR showed that the desired ketosulfone has formed to the extent of 80%. The ether layer was separated, dried over NaSO4, evaporated and chromatographed over silica (20% ethyl acetate in hexane) to yield the title compound after crystallization from ether: NMR (200 MHz, CDCl3) δ 0.98 (t, CH2CH2CH3), 1.83 (m, CH2CH2CH3), 1.9-2.6 (m, 3-CH2 δ4-CH2), 2.38 (s, CH3C(O)CH 2), 3.86 (s, OCH3), 3.88 (s, 2 OCH3), 4.18 (t, OCH2CH2CH3), 4.48 (s, CH3C(O)CH2), 5.18 (s, OCH2Ar), 5.06-5.28 (m, 2-CH δ 5-CH), 6.61 (s, 5-ArH), 7.32-7.54 (m, ArH).

Aufarbeitung

  1. temperaturewas cooled to -78°
  2. additionwas added
  3. customhas formed to the extent of 80%
  4. customThe ether layer was separated
  5. dry with materialdried over NaSO4
  6. customevaporated
  7. customchromatographed over silica (20% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-20025d70f3f64e86986bb3d957c5f53f
Quelldatensatz
uspto-grants-1992_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05114961

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