4,4'-Di-3,5-hexadienoxybenzophenone → 4,4'-Di-3,5-hexadienoxytrityl alcohol

HRID 611749Notes

Reaction equation

HRID 611749 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][CH2:22][CH:23]=[CH:24][CH:25]=[CH2:26])=[CH:16][CH:15]=2)=[O:13])=[CH:10][CH:9]=1)[CH2:2][CH:3]=[CH:4][CH:5]=[CH2:6].[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][CH2:22][CH:23]=[CH:24][CH:25]=[CH2:26])=[CH:18][CH:19]=2)=[CH:10][CH:9]=1)[CH2:2][CH:3]=[CH:4][CH:5]=[CH2:6]

Participants

4

Reactant 2

HCID 542346134,4'-Di-3,5-hexadienoxybenzophenoneHCID 178418255HCID 178418255, compound

Product 1

HCID 538662944,4'-Di-3,5-hexadienoxytrityl alcoholYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Compound 29 (5.96 g, 15.91 mmol) was dissolved in anhydrous THF (133 mL) with slight heating. Phenylmagnesium bromide (32 mL of a 1.0 M solution in THF, 32 mmol) was added to the solution and the mixture was stirred at room temperature under argon for 5 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 by column chromatography (silica gel; hexane/CH2Cl2, 1/9) to yield 4.45 grams (62%) of compound 30 as a yellow oil. 1H NMR (300 MHz, DMSO-d6)δ 2.45-2.56 (m, 4H), 3.98 (t, J=6.6 Hz, 4H), 5.01 (dd, J=1.5, 9.9 Hz, 2H), 5.14 (dd, J=1.5, 16.5 Hz, 2H), 5.73-5.87 (m, 2H), 6.12-6.41 (m, 4H), 6.25 (s, 1H), 6.84 (d, J=6.9 Hz, 4H), 7.06 (d, J=7.8 Hz, 4H), 7.15-7.33 (m, 5H).

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 by column chromatography (silica gel; hexane/CH2Cl2, 1/9)

Sources & evidence

ORD record
ord-536a0f9bfad34d7d830f0693048f931e
Source dataset
uspto-grants-1999_12
Patent number
US06001966

Reaction notes

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