Tetrahydrofuran → HCID 66838732, compound

HRID 2066001Notes

Reaction equation

HRID 2066001 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([Mg]Br)=[CH:4][CH:3]=1.[CH2:10]1[CH2:14][O:13][CH2:12][CH2:11]1.C(OCC)(=[O:17])C.C1CCCCC1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:10]([OH:17])([CH3:14])[CH2:11][CH2:12][OH:13])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 21867204Cyclohexane ethylacetateHCID 178418676HCID 178418676, compound

Product 1

HCID 66838732HCID 66838732, compound

Procedure

The molecular sieves were removed by filtration. At a temperature of −60° C. 13 mL of 0.83M 4-fluorophenylmagnesium bromide in THF (10.8 mmol, 2.00 eq) were added. The conversion was determined by TLC (eluent: ethyl acetate/cyclohexane 1+1). The reaction was quenched after 45 minutes by addition of 10 mL of 2.5M aqueous NaOH. The layers were separated and the organic layer was washed twice with 10 mL of 1M aqueous KHSO4, and once with 10 mL of sat. aqueous NaHCO3.

Workup

  1. customThe molecular sieves were removed by filtration
  2. customAt a temperature of −60° C
  3. customThe reaction was quenched after 45 minutes by addition of 10 mL of 2.5M aqueous NaOH
  4. customThe layers were separated
  5. washthe organic layer was washed twice with 10 mL of 1M aqueous KHSO4

Sources & evidence

ORD record
ord-2d6146a2725e4fc29f707b98771c2fa0
Source dataset
uspto-grants-2012_10
Patent number
US08288569B2

Reaction notes

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