Tetrahydrofuran → HCID 15661459, compound

HRID 1707985Notes

Reaction equation

HRID 1707985 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]1[C:21]2[C:20](=[O:22])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]=2[CH:12]=[C:11]([C:23]([C:25]2C=CC=CN=2)=S)[CH:10]=1.C[Mg+].[Br-].C1C[O:37]CC1>>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]1[C:21]2[C:20](=[O:22])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]=2[CH:12]=[C:11]([C:23]([CH3:25])=[O:37])[CH:10]=1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 18960549HCID 18960549, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 15661459HCID 15661459, compound

Conditions

Temperature
-10 °C

Procedure

1-(2-Tetrahydropyranyl)oxymethyl-3-(2-pyridyl)thiocarbonyl-9-fluorenone (470 mg) was dissolved in THF (10 ml) and cooled to -15° under N2. A solution of MeMgBr in THF (1.2 eq) was added dropwise over 5 min and the reaction allowed to stir at -10° C. for 0.5 hr. The reaction was quenched with saturated ammonium chloride solution, diluted with EtOAc, and washed with water, sat'd NaCl sol'n then dried and evaporated which gave a residue which was chromatographed on silica gel to give the product (233 mg).

Workup

  1. temperaturecooled to -15° under N2
  2. customThe reaction was quenched with saturated ammonium chloride solution
  3. additiondiluted with EtOAc
  4. washwashed with water
  5. customsol'n then dried
  6. customevaporated which
  7. customgave a residue which
  8. customwas chromatographed on silica gel

Sources & evidence

ORD record
ord-6ccb7c667e9c4806a29f5e31aa125b03
Source dataset
uspto-grants-1994_10
Patent number
US05356889

Reaction notes

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