Tetrahydrofuran → HCID 66709635, compound

HRID 1193028Notes

Reaction equation

HRID 1193028 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.C([Li])CCC.[CH2:11]([O:18][C:19]1[CH:26]=[C:25]([CH3:27])[C:22](C=O)=[C:21]([CH3:28])[CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Cl-].[NH4+].[O:31]1CCC[CH2:32]1>>[CH2:11]([O:18][C:19]1[CH:26]=[C:25]([CH3:27])[C:22]([C:3]2[CH:4]=[CH:5][O:1][C:2]=2[CH2:32][OH:31])=[C:21]([CH3:28])[CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 8029FuranHCID 25517Ammonium ChlorideHCID 111608034-(Benzyloxy)-2,6-dimethylbenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 66709635HCID 66709635, compound

Conditions

Temperature
-78 °C

Procedure

To a solution of furan (10.9 ml, 150 mmol) in dry tetrahydrofuran (200 ml) is added dropwise, under nitrogen, n-butyllithium (2.5 M solution in hexane, 50 ml, 125 mmol) at −78° C. When the addition is complete, the reaction is stirred for 30 minutes at −78° C. A solution of 4-benzyloxy-2,6-dimethylbenzaldehyde (23.0 g, 96 mmol) in dry tetrahydrofuran (100 ml) is added dropwise over 30 minutes. On completion of the addition, the reaction is allowed to warm to room temperature and stirring is continued for 2 hours. A solution of saturated aqueous ammonium chloride solution (300 ml) is added and the reaction mixture is extracted with dichloromethane (3×250 ml). The organic extract are combined, washed with brine, dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated under reduced pressure. The product, ([4-benzyloxy-2,6-dimethylphenyl]furan-2-yl)methanol (32 g) is used without further purification in the next step.

Workup

  1. customat −78° C
  2. additionWhen the addition
  3. additionOn completion of the addition
  4. temperatureto warm to room temperature
  5. stirringstirring
  6. waitis continued for 2 hours
  7. extractionthe reaction mixture is extracted with dichloromethane (3×250 ml)
  8. extractionThe organic extract
  9. washwashed with brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. filtrationfiltered
  12. customthe filtrate is evaporated under reduced pressure
  13. customThe product, ([4-benzyloxy-2,6-dimethylphenyl]furan-2-yl)methanol (32 g) is used without further purification in the next step

Sources & evidence

ORD record
ord-e98f9b77ba644fe2ae3bb62d01288f92
Source dataset
uspto-grants-2014_03
Patent number
US08680339B2

Reaction notes

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