Tetrahydrofuran → HCID 86625050, compound

HRID 1642643Notes

Reaction equation

HRID 1642643 reaction equation
[CH2:1]([O:8][C:9]1[C:17](Br)=[CH:16][C:15]([CH3:19])=[C:14]2[C:10]=1[CH2:11][CH2:12][CH2:13]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li]CCCC.C1C[O:28][CH2:27]C1>>[CH2:1]([O:8][C:9]1[C:17]([CH:27]=[O:28])=[CH:16][C:15]([CH3:19])=[C:14]2[C:10]=1[CH2:11][CH2:12][CH2:13]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 66756725HCID 66756725, compoundHCID 178418339Butyllithium

Product 1

HCID 86625050HCID 86625050, compound

Conditions

Temperature
-78 °C

Procedure

To a solution of 4-benzyloxy-5-bromo-7-methylindan (5.87 g, 19.4 mmol) in THF (75 mL) at −78° C. is added dropwise n-BuLi (1.6 M in hexane, 13.3 mL, 21.3 mmol) and it is stirred at −78° C. for 1.5 h. DMF (freshly distilled from CaH2, 29 mL, 0.38 mol) is added dropwise and it is stirred at −78° C. for 4 h before slowly warmed to ambient temperature and stirred for 18 h. EtOAc is added and it is washed with 1N HCl and brine, dried and concentrated. The residue is purified by flash chromatography to give the title compound as a light yellow solid.

Workup

  1. distillationDMF (freshly distilled from CaH2, 29 mL, 0.38 mol)
  2. additionis added dropwise
  3. stirringit is stirred at −78° C. for 4 h
  4. temperaturebefore slowly warmed to ambient temperature
  5. stirringstirred for 18 h
  6. additionEtOAc is added
  7. washit is washed with 1N HCl and brine
  8. customdried
  9. concentrationconcentrated
  10. customThe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-b56b90de3f0a4bcf900f8d28ce402d33
Source dataset
uspto-grants-2012_02
Patent number
US08119666B2

Reaction notes

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