Hydrochloric Acid → HCID 68469064, compound

HRID 641587Notes

Reaction equation

HRID 641587 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([S:11][CH3:12])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[Li]CCCC.B(F)(F)F.CCOCC.[O:27]1[CH:33]2[CH:28]1[CH2:29][O:30][CH2:31][CH2:32]2.Cl>C1COCC1.CCCCCC.CCOC(C)=O>[CH3:12][S:11][C:8]1[CH:9]=[CH:10][C:5]([S:2]([CH2:1][C@@H:33]2[CH2:32][CH2:31][O:30][CH2:29][C@H:28]2[OH:27])(=[O:4])=[O:3])=[CH:6][CH:7]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 8000Boron trifluoride etherateHCID 44016291-Methanesulfonyl-4-methylsulfanyl-benzeneHCID 120221313,7-Dioxabicyclo(4.1.0)heptaneHCID 178418339Butyllithium

Product 1

HCID 68469064HCID 68469064, compoundYield 20.2%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

1-Methanesulfonyl-4-methylsulfanyl-benzene (4.3 g) was dissolved in THF (40 ml) and cooled to −78° C. prior to the slow addition of 1.6 M n-BuLi in hexane (13.4 ml). After 0.5 h, BF3.Et2O (2.7 ml) was added followed by 3,4-epoxytetrahydropyran (2.2 g) (Berti et al. Tetrahedron 1974, 30, 4013) (2.3 g) in THF (20 ml). After an addition 1 h at −78° C., the solution was warmed to 0° C. After 2 h, the solution was cooled to −78° C. and 1N HCl solution (aq) was added. The solution was warmed to rt and EtOAc was added. The organic layer was washed with brine, dried, filtered, and concentrated. Flash chromatography of the resulting residue gave (3S*,4R*)-4-(4-methylsulfanyl-benzenesulfonylmethyl)-tetrahydro-pyran-3-ol (1.3 g) as the major product. MS found: (M+H)+=303.0.

Workup

  1. additionAfter an addition 1 h at −78° C.
  2. temperaturethe solution was warmed to 0° C
  3. waitAfter 2 h
  4. temperaturethe solution was cooled to −78° C.
  5. temperatureThe solution was warmed to rt
  6. washThe organic layer was washed with brine
  7. customdried
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-9dec72b6065c411db3fb4d3b4c4f8415
Source dataset
uspto-grants-2010_04
Patent number
US07696205B2

Reaction notes

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