Sodium Chloride → HCID 12967235, compound

HRID 1610042Notes

Reaction equation

HRID 1610042 reaction equation
C(NC(C)C)(C)C.CCCCCC.C([Li])CCC.[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH:36]=[CH:37][CH:38]=1)[CH2:24][O:25][CH2:26][C:27]([CH3:35])([CH3:34])[C:28](=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30].[Cl-].[Na+]>C1COCC1>[C:29]([C:28]1([OH:33])[C:27]([CH3:35])([CH3:34])[CH2:26][O:25][CH:24]1[C:23]1[CH:36]=[CH:37][CH:38]=[C:21]([O:20][CH3:19])[CH:22]=1)([CH3:31])([CH3:32])[CH3:30]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 7912DiisopropylamineHCID 11076774HCID 11076774, compound2×HCID 178418244HCID 178418244, compound

Product 1

HCID 12967235HCID 12967235, compoundYield 87.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a nitrogen atmosphere, 1.50 ml (11.4 mmol) of diisopropylamine and 6.60 ml (10.6 mmol) of a 1.6 M butyl lithium hexane solution, were added to 15 ml of anhydrous THF at room temperature, followed by stirring for 30 minutes. To this solution, 1.48 g (5.32 mmol) of 1-(3-methoxybenzyloxy)-2,2,4,4-tetramethyl-3-pentanone (compound (4)) dissolved in 10 ml of THF, was added at −78° C., followed by stirring for 2 hours. The reaction solution was gradually heated to room temperature and stirred for 3 hours and 20 minutes. The reaction mixture was put into a saturated sodium chloride aqueous solution and extracted with ethyl acetate. The extract layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and then concentrated. The concentrated product was subjected to a silica gel column and eluted with a 1:2 mixed solvent of hexane and ethyl acetate, to obtain 1.30 g of 3-t-butyl-3-hydroxy-2-(3-methoxyphenyl)-4,4-dimethyl-2,3,4,5-tetrahydrofuran (compound (5)) in a yield of 87.8%. Melting point: 83.0–83.5° C. (colorless granular crystals, recrystallized from hexane and ethyl acetate)

Workup

  1. additionwas added at −78° C.
  2. stirringby stirring for 2 hours
  3. stirringstirred for 3 hours and 20 minutes
  4. extractionextracted with ethyl acetate
  5. washThe extract layer was washed with a saturated sodium chloride aqueous solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. washeluted with a 1:2 mixed solvent of hexane and ethyl acetate

Sources & evidence

ORD record
ord-1120743634cb439c9152e793fde57e48
Source dataset
uspto-grants-2006_01
Patent number
US06982336B2

Reaction notes

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