4,4'-Di-2,4-hexadienoxybenzophenone → 4,4'-Di-2,4-hexadienoxytrityl alcohol

HRID 1385481Notes

Reaction equation

HRID 1385481 reaction equation
[CH2:1]([O:7][C:8]1[CH:28]=[CH:27][C:11]([C:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH:22]=[CH:23][CH:24]=[CH:25][CH3:26])=[CH:16][CH:15]=2)=[O:13])=[CH:10][CH:9]=1)[CH:2]=[CH:3][CH:4]=[CH:5][CH3:6].[C:29]1([Mg]Br)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C1COCC1>[CH2:1]([O:7][C:8]1[CH:28]=[CH:27][C:11]([C:12]([OH:13])([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:14]2[CH:15]=[CH:16][C:17]([O:20][CH2:21][CH:22]=[CH:23][CH:24]=[CH:25][CH3:26])=[CH:18][CH:19]=2)=[CH:10][CH:9]=1)[CH:2]=[CH:3][CH:4]=[CH:5][CH3:6]

Participants

4

Reactant 2

HCID 538753704,4'-Di-2,4-hexadienoxybenzophenoneHCID 178418255HCID 178418255, compound

Product 1

HCID 538212704,4'-Di-2,4-hexadienoxytrityl alcoholYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 35 (2.0 grams) was dissolved in THF (45 mL) and phenylmagnesium bromide (1.0 M solution in THF; 10.6 mL, 10.6 mmol) was added to the solution. The reaction mixture was stirred at room temperature for 3 hours, and evaporated to dryness under vacuum. The residue was redissolved in dichloromethane and washed with a saturated solution of ammonium chloride, followed by water. The organic phase was dried (MgSO4), concentrated in vacuo and purified column chromatography (silica gel; hexane/CH2Cl2, 1/9) to afford 1.84 grams (77%) of compound 36 as a pale yellow solid. 1H NMR (300 MHz, DMSO-d6) δ 1.73 (d, J=6.9 Hz, 6 H), 4.54 (d, J=6.0 Hz, 4 H), 5.68-5.80 (m, 4 H), 6.02, 6.11 (m, 2 H), 6.20-6.37 (m, 2 H), 6.85 (d, J=6.9 Hz, 4 H), 7.05 (d, J=7.0 Hz, 4 H), 7.14-7.32 (m, 5 H); Anal. Calcd for C31H32O3 (452.5920): C, 82.27; H, 7.13; Found: C, 82.30; H, 7.11.

Workup

  1. customevaporated to dryness under vacuum
  2. dissolutionThe residue was redissolved in dichloromethane
  3. washwashed with a saturated solution of ammonium chloride
  4. dry with materialThe organic phase was dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. custompurified column chromatography (silica gel; hexane/CH2Cl2, 1/9)

Sources & evidence

ORD record
ord-45c3f3f079bc4b8c987753694e3f9940
Source dataset
uspto-grants-2001_07
Patent number
US06262251B1

Reaction notes

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