Fluoride Ion → 6-(2-Cyclopentyl-2-hydroxy-but-3-ynyl)-2,2-dimethyl-[1,3]dioxin-4-one

HRID 859617Notes

Reaction equation

HRID 859617 reaction equation
[CH:1]1([C:6]([OH:23])([C:17]#[C:18][Si](C)(C)C)[CH2:7][C:8]2[O:13][C:12]([CH3:15])([CH3:14])[O:11][C:10](=[O:16])[CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[F-]>CO>[CH:1]1([C:6]([OH:23])([C:17]#[CH:18])[CH2:7][C:8]2[O:13][C:12]([CH3:15])([CH3:14])[O:11][C:10](=[O:16])[CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 28179Fluoride IonHCID 224997936-(2-Cyclopentyl-2-hydroxy-4-trimethylsilanyl-but-3-ynyl)-2,2-dimethyl-[1,3]dioxin-4-one

Product 1

HCID 224998026-(2-Cyclopentyl-2-hydroxy-but-3-ynyl)-2,2-dimethyl-[1,3]dioxin-4-oneYield 54.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of crude 6-[2-cyclopentyl-2-hydroxy-4-(trimethylsilyl)but-3-yn-1-yl]-2,2-dimethyl-4H-1,3-dioxin-4-one (25 mmol), ceasium fluoride (7.6 g, 50 mmol) dissolved in MeOH (75 mL) was stirred over night. The solvent was removed and the residue was diluted with EtOAc, washed with 0.5 N citric acid, 1 N NaHCO3, brine, dried over MgSO4 and concentrated. Purification by flash column chromatography (20% to 30% EtOAc in hexanes) gave the product (3.6 g, 54%). 1H NMR (300 MHz, CDCl3) □: 1.45–1.80 (m, 8 H), 1.72 (s, 3 H), 1.74 (s, 3 H), 2.13–2.18 (m, 1 H), 2.49 (s, 1 H), 2.56 (s, 1 H), 2.58 (s, 2 H), 5.43 (s, 1 H).

Workup

  1. customThe solvent was removed
  2. additionthe residue was diluted with EtOAc
  3. washwashed with 0.5 N citric acid, 1 N NaHCO3, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customPurification by flash column chromatography (20% to 30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-40b32daf44164437a4d03253c4a60a28
Source dataset
uspto-grants-2006_12
Patent number
US07151105B2

Reaction notes

Loading…