Boron trifluoride → HCID 68469064, compound

HRID 502932Notes

Reaction equation

HRID 502932 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.[O:22]1[CH:28]2[CH:23]1[CH2:24][O:25][CH2:26][CH2:27]2.[NH4+].[Cl-]>C1COCC1.CCOC(C)=O.CCOCC>[CH3:12][S:11][C:8]1[CH:9]=[CH:10][C:5]([S:2]([CH2:1][C@@H:28]2[CH2:27][CH2:26][O:25][CH2:24][C@H:23]2[OH:22])(=[O:4])=[O:3])=[CH:6][CH:7]=1

Participants

9

Reactant 5

HCID 6356Boron trifluorideHCID 25517Ammonium ChlorideHCID 44016291-Methanesulfonyl-4-methylsulfanyl-benzeneHCID 120221313,7-Dioxabicyclo(4.1.0)heptaneHCID 178418339Butyllithium

Product 1

HCID 68469064HCID 68469064, compoundYield 35.9%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

1-Methanesulfonyl-4-methylsulfanyl-benzene (4.33 g) was dissolved in THF (50 mL) and cooled to −78° C. prior to the addition of 1.6 M nBuLi (13.4 mL). After 0.5 h, BF3. Et2O (2.7 mL) was added followed (±)3,4-epoxytetrahydropyran (1.2 g) (Tetrahedron 1974, 4013). 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 saturated NH4Cl 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-06330c64835842568409d0c111e152d2
Source dataset
uspto-grants-2010_08
Patent number
US07776884B2

Reaction notes

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