tert-Butanol → HCID 13755108, compound

HRID 2298724Notes

Reaction equation

HRID 2298724 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7]C(/C=C/C(OC)=O)=[CH:5][CH:4]=1.C[N+]1([O-])CC[O:19]CC1.[C:23]([OH:27])([CH3:26])([CH3:25])C.C1C(O)=C(O)C(S([O-])(=O)=O)=CC=1S([O-])(=O)=O.[Na+].[Na+].[C:46]([O:49][CH2:50]C)(=[O:48])C>O.O.[O-][Os]([O-])(=O)=O.[K+].[K+].O>[OH:19][CH:25]([CH:23]([OH:27])[C:26]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)[C:46]([O:49][CH3:50])=[O:48]

Participants

8

Reactant 5

HCID 6386tert-ButanolHCID 8857Ethyl AcetateHCID 9001149-45-1HCID 82029Methyl morpholine oxideHCID 641297(E)-Methyl 3-(4-methoxyphenyl)acrylate

Product 1

HCID 13755108HCID 13755108, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 53393272Potassium osmate(VI) dihydrateCatalystHCID 962WaterSolvent

Procedure

[DHQD]2PHAL (54.5 mg, 0.25 mol %), methyl (E)-3-(4-methoxyphenyl)-2-propenoate (5.38 g, 28 mmol), N-methyl morpholine N-oxide (60% aqueous solution, 7.0 ml) and tert-butanol (11.2 ml) were charged to a 100 ml 3-neck flask and stirred at room temperature. Potassium osmate (VI) dihydrate (21.4 mg, 0.2 mol %) was added portionwise and the reaction was stirred at room temperature. The reaction procedure was monitored by HPLC. After 17 hours, Tiron (200 mg) was added to quench the reaction, followed by water (50 ml). The mixture was allowed to stir for one hour, ethyl acetate (50 ml) was added to the mixture and the resultant two layers were vigorously stirred for 30 minutes. The organic phase was removed and washed with water, dried (Na2SO4) and evaporated to dryness on a rotary evaporator. The product was purified by flash column chromatography using DCM: ethyl acetate (3:2) as eluant. Evaporation of the appropriate fractions gave methyl 2,3-dihydroxy-3- (4-methoxyphenyl)propanoate as a white crystalline solid (3.2 g, 62%). mp. 108° C., [α]D=−1.2° (THF, conc.=0.01306 22° C.). 1H-NMR was in accordance with expected signals.

Workup

  1. stirringthe reaction was stirred at room temperature
  2. customThe reaction procedure
  3. customto quench
  4. customthe reaction
  5. stirringto stir for one hour
  6. stirringthe resultant two layers were vigorously stirred for 30 minutes
  7. customThe organic phase was removed
  8. washwashed with water
  9. dry with materialdried (Na2SO4)
  10. customevaporated to dryness on a rotary evaporator
  11. customThe product was purified by flash column chromatography
  12. customEvaporation of the appropriate fractions

Sources & evidence

ORD record
ord-7e14f988d9954a898f49be48471e43b1
Source dataset
uspto-grants-2002_12
Patent number
US06495217B2

Reaction notes

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