Water → (6-Methyl-1,3-dihydroisobenzofuran-5-yl)methanol

HRID 2047261Notes

Reaction equation

HRID 2047261 reaction equation
[Li].C(C1C=CC(C2C=CC(C(C)(C)C)=CC=2)=CC=1)(C)(C)C.[C:22]12[CH2:33][O:32][CH2:31][C:30]1=[CH:29][C:28]1[CH2:27][O:26][CH2:25][C:24]=1[CH:23]=2.O>O1CCCC1>[CH3:33][C:22]1[C:30]([CH2:31][OH:32])=[CH:29][C:28]2[CH2:27][O:26][CH2:25][C:24]=2[CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 741954,4'-Bis(1,1-dimethylethyl)-1,1'-biphenylHCID 3028194LithiumHCID 595388301,3,5,7-Tetrahydrobenzo[1,2-c:4,5-c']difuran

Product 1

HCID 86691253(6-Methyl-1,3-dihydroisobenzofuran-5-yl)methanolYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of lithium powder (15 g, 2.1 mol), 4,4′-di-tert-butylbiphenyl (5.0 g, 0.021 mol) and tetrahydrofuran (200 mL) was added a mixture of 5,11-dioxatricyclo[7.3.0.0^{3,7}]dodeca-1,3(7),8-triene (35 g, 0.21 mol) described in Production Example 1-4 and tetrahydrofuran (100 mL) at −78° C., followed by stirring at that temperature for 4 hours. Water (10 mol) was added at that temperature to the reaction mixture, and thoroughly stirred. The reaction mixture was allowed to warm to room temperature, and extracted with ethyl acetate after addition of a 2 N aqueous solution of hydrochloric acid (500 mL). The organic layer was washed with brine and dried over anhydrous sodium sulfate, and the solvent was distilled away under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=3:7) to give the title compound (10 g, 30% yield).

Workup

  1. additionwas added
  2. stirringthoroughly stirred
  3. extractionextracted with ethyl acetate
  4. additionafter addition of a 2 N aqueous solution of hydrochloric acid (500 mL)
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled away under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=3:7)

Sources & evidence

ORD record
ord-0907c14d27a24928a1e50065e6f25dc8
Source dataset
uspto-grants-2013_11
Patent number
US08592470B2

Reaction notes

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