Benzophenone → HCID 15599366, compound

HRID 986425Notes

Reaction equation

HRID 986425 reaction equation
[I-].[CH2:2]([O:9][C:10]1[C:11]([CH2:19]P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:12][C:13]2[O:17][CH2:16][CH2:15][C:14]=2[CH:18]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([Li])CCC.[C:44]([C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)(=O)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>O1CCCC1>[CH2:2]([O:9][C:10]1[C:11]([CH:19]=[C:44]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)=[CH:12][C:13]2[O:17][CH2:16][CH2:15][C:14]=2[CH:18]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 3102BenzophenoneHCID 178418339ButyllithiumHCID 178506546HCID 178506546, compound

Product 1

HCID 15599366HCID 15599366, compoundYield 22.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of (5-benzyloxy-2,3-dihydro-benzofuran-6-yl)methyl triphenylphosphine iodide (2.0 g, 0.0033 mol) in tetrahydrofuran (20 ml) was cooled to an internal temperature of 5° C. under nitrogen and a solution of n-butyllithium (1.55M in hexane, 1.9 ml, 0.0030 mol) was added dropwise. The resulting mixture was stirred for 10 minutes then benzophenone (0.47 g, 0.0030 mol) was added portionwise. The ice bath was removed and the reaction was allowed to stir for 18 hours, then heated to reflux for 4 hours. The reaction mixture was concentrated to a dark oil which was dissolved in ethyl acetate (20 ml), washed with water (10 ml), saturated sodium chloride (10 ml). The combined organic layers were dried (MgSO4), concentrated then chromatographed over silica gel (hexane/ethyl acetate, 90/10, an eluent) to afford 1-(5-benzyloxy-2,3-dihydrobenzofuran-6-yl)-2,2-diphenyl-ethene (0.27 g, 22%).

Workup

  1. customThe ice bath was removed
  2. stirringto stir for 18 hours
  3. temperatureheated
  4. temperatureto reflux for 4 hours
  5. concentrationThe reaction mixture was concentrated to a dark oil which
  6. dissolutionwas dissolved in ethyl acetate (20 ml)
  7. washwashed with water (10 ml), saturated sodium chloride (10 ml)
  8. dry with materialThe combined organic layers were dried (MgSO4)
  9. concentrationconcentrated
  10. customthen chromatographed over silica gel (hexane/ethyl acetate, 90/10

Sources & evidence

ORD record
ord-690509bfd6424a40ae7391c7ddfd134d
Source dataset
uspto-grants-1987_12
Patent number
US04713393

Reaction notes

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