Potassium Carbonate → [8-Methyl-2,3-dihydrofuro[3,2-f][1,4]benzodioxin-2-yl]methanol

HRID 1267240Notes

Reaction equation

HRID 1267240 reaction equation
Cl[C:2](=[CH2:17])[CH2:3][C:4]1[C:13]2[O:12][C@@H:11]([CH2:14][OH:15])[CH2:10][O:9][C:8]=2[CH:7]=[CH:6][C:5]=1[OH:16].C(=O)([O-])[O-].[K+].[K+]>FC(F)(F)C(O)=O>[CH3:17][C:2]1[O:16][C:5]2[CH:6]=[CH:7][C:8]3[O:9][CH2:10][CH:11]([CH2:14][OH:15])[O:12][C:13]=3[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86586531(3S)-5-(2-chloro-2-propenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-ol

Product 1

HCID 18546026[8-Methyl-2,3-dihydrofuro[3,2-f][1,4]benzodioxin-2-yl]methanol

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 0.40 g (1.6 mmole) of (3S)-5-(2-chloro-2-propenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-ol in 70 mL of trifluoroacetic acid was stirred at room temperature for 26 hours. The solvent was then removed in vacuum and replaced with 100 mL of methanol. Potassium carbonate (3.0 g, 2.2 mmole) was added and the mixture stirred for an additional 1.5 hours at room temperature. The mixture was then filtered and the filtrate concentrated to a brown residue in vacuum. The residue was column chromatographed on silica gel with methylene chloride as eluant to give 0.20 g (60%) of the (S)-enantiomer of the title compound as a yellow oil. 1H-NMR (d6-DMSO): doublet 6.94 δ (1H); doublet 6.71 δ (1H); singlet 6.48 δ (1H); triplet 5.07 δ (1H); doublet of doublets 4.30 δ (1H); multiplet 4.22 δ (1H); multiplet 4.00 δ (1H); multiplet 3.65 δ (2H); singlet 2.38 δ (3H).

Workup

  1. customThe solvent was then removed in vacuum
  2. filtrationThe mixture was then filtered
  3. concentrationthe filtrate concentrated to a brown residue in vacuum
  4. customchromatographed on silica gel with methylene chloride as eluant

Sources & evidence

ORD record
ord-7e7aa7303d5347d3a73093d98ad596f4
Source dataset
uspto-grants-2003_04
Patent number
US06552049B2

Reaction notes

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