2-(2-Methylallyl)propane-1,3-diol → Tetrahydro-5,5-dimethyl-3-furanmethanol

HRID 709800Notes

Reaction equation

HRID 709800 reaction equation
[CH3:1][C:2](=[CH2:9])[CH2:3][CH:4]([CH2:7][OH:8])[CH2:5][OH:6]>ClCCl.FC(F)(F)S([O-])(=O)=O.[Ag+]>[CH3:9][C:2]1([CH3:1])[O:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3]1

Participants

4

Reactant 1

HCID 152978952-(2-Methylallyl)propane-1,3-diol

Product 1

HCID 15365931Tetrahydro-5,5-dimethyl-3-furanmethanolYield 100%

Reagents, catalysts & solvents 2

HCID 76223Silver(I) trifluoromethanesulfonateCatalystHCID 6344DichloromethaneSolvent

Procedure

Under a nitrogen atmosphere, a solution of 2-(2-methylallyl)propane-1,3-diol (2.00 g) and silver trifluoromethanesulfonate (197 mg) in dichloromethane (40 mL) was stirred at 80° C. for 2 days. The reaction mixture was filtered through celite, and the filtrate was evaporated under reduced pressure to give the title compound (2.00 g) as a brown oil. This compound was used for the next step without further purification.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-08e1407088be404c8bd858251f497980
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

Loading…