Tetrahydrofuran → HCID 21202063, compound

HRID 1978876Notes

Reaction equation

HRID 1978876 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=1[CH2:12][CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:2]C.C1C[O:24]CC1>O.[Os](=O)(=O)(=O)=O>[O:24]=[CH:2][CH2:1][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=1[CH2:12][CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 70097299HCID 70097299, compound

Product 1

HCID 21202063HCID 21202063, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent

Procedure

To a solution of tert-butyl 3-(2-propeny-5-methoxyphenyl)propionate (7.2 g, 26 mmol) in THF (60 mL) and H2O (30 mL) were added NaO4 (9.8 g, 46 nmmol) and 4% osmium tetroxide (1 mL). After stirring at RT, the mixture was filtered and the filtrate was diluted with ether. The combined extracts were dried and evaporated to give the crude product which was flash chromatographed to give the titled compound (3.0 g; 43% yield).

Workup

  1. filtrationthe mixture was filtered
  2. additionthe filtrate was diluted with ether
  3. customThe combined extracts were dried
  4. customevaporated
  5. customto give the crude product which
  6. customchromatographed

Sources & evidence

ORD record
ord-fe7398e0a59d49dfadf68c0536ddb150
Source dataset
uspto-grants-2001_05
Patent number
US06239138B1

Reaction notes

Loading…