Diethyl Ether → (1S,4R)-4-{[Tert-butyl(dimethyl)silyl]oxy}-2-cyclopenten-1-YL acetate

HRID 2393899Notes

Reaction equation

HRID 2393899 reaction equation
[Si:1]([O:8][C@@H:9]1[CH2:13][C@H:12]([OH:14])[CH:11]=[CH:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:15](OC(=O)C)(=[O:17])[CH3:16].C(OCC)C.C(OCC)(=O)C.CCCCCC>N1C=CC=CC=1.C(Cl)(Cl)Cl>[Si:1]([O:8][C@@H:9]1[CH2:13][C@H:12]([O:14][C:15](=[O:17])[CH3:16])[CH:11]=[CH:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 7918Acetic AnhydrideHCID 101767472-Cyclopenten-1-ol, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, cis-HCID 21226206Ethyl acetate hexane

Product 1

HCID 10999690(1S,4R)-4-{[Tert-butyl(dimethyl)silyl]oxy}-2-cyclopenten-1-YL acetateYield 98%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent

Procedure

Dissolve (-)-cis-4-tert-butyldimethylsilyloxy-2-cyclopentenol (1 9, 4.67 mmol, prepared in example 10) in pyridine (20 mL) and treat with acetic anhydride (2 mL). Stir the reaction overnight. Dilute the reaction with diethyl ether (100 mL), wash with 3M hydrochloric acid (3×100 mL), saturated sodium bicarbonate (100 mL), brine (100 mL), dry over anhydrous magnesium sulfate, filter and concentrate under vacuum to provide the title compound (1 g, 98% yield), Rf =0.5 (5% ethyl acetate/hexane), [α]20D =+1.3°, (c=1.00, chloroform), 1H NMR (CDCl3) δ 5.9 (m, 1 H), 5.5 (m, 1 H), 4.7 (m, 1 H), 2.8 (m, 1 H), 2.05 (s, 3 H), 1.6 (m, 1 H), 0.91 (s, 9 H), 0.09 (s, 6 H); 13C NMR (CDCl3) δ 170.8, 138.8, 131.1, 76.9, 74.8, 41.1, 25.8, 21.1, 18.1, -4.7, -4.6; IR (neat) νmax 2955, 2932, 2859, 1739, 1369, 1240, 1105, 1062, 1049 cm-1 ; CIMS m/e (% relative intensity) 256 (M+H+, 7), 197 (M+H+ --AcOH, 100).

Workup

  1. customthe reaction overnight
  2. additionDilute
  3. washwash with 3M hydrochloric acid (3×100 mL), saturated sodium bicarbonate (100 mL), brine (100 mL)
  4. dry with materialdry over anhydrous magnesium sulfate
  5. filtrationfilter
  6. concentrationconcentrate under vacuum

Sources & evidence

ORD record
ord-c69df6912e2b4f3f9241935ca8c31848
Source dataset
uspto-grants-1998_09
Patent number
US05808112

Reaction notes

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