Tetrabutylammonium Fluoride → HCID 11768599, compound

HRID 1779992Notes

Reaction equation

HRID 1779992 reaction equation
[CH3:1][C@@H:2]1[C@@H:7]([CH2:8][O:9][Si](C(C)(C)C)(C)C)[O:6][C:4](=[O:5])[CH2:3]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:1][C@@H:2]1[C@@H:7]([CH2:8][OH:9])[O:6][C:4](=[O:5])[CH2:3]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 102292925HCID 102292925, compound

Product 1

HCID 11768599HCID 11768599, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,3-Dideoxy-3-C-methyl-5-O-tert-butyldimethylsilyl-D-erythro-pentono-1,4-lactone (1.4 g, 6.13 mmol) was treated with tetra-n-butylammonium fluoride (8.7 mL of a 1.0M solution in tetrahydrofuran, 8.7 mmol) for 90 minutes at room temperature. The reaction mixture was evaporated, and the crude product subjected to flash silica gel chromatography eluting initially with 15% acetone in hexane and subsequently with 25% acetone in hexane. Pure title compound was obtained as an oil; yield 710 mg (89%); 1H NMR (400 MHz, CDCl3): δ1.16 (d, 3H), 2.21 (dd, 1H), 2.50 (m, 1H), 2.72 (dd, 1H).

Workup

  1. customThe reaction mixture was evaporated
  2. washeluting initially with 15% acetone in hexane and subsequently with 25% acetone in hexane

Sources & evidence

ORD record
ord-b43c28c9f96a481fb209bdce0c4683a9
Source dataset
uspto-grants-1997_05
Patent number
US05629322

Reaction notes

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