Tetrabutylammonium Fluoride → 1-(7-Methoxybenzofuran-2-yl)-butane-1,4-diol

HRID 2270114Notes

Reaction equation

HRID 2270114 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][CH2:27][CH2:28][CH2:29][CH:30]([C:32]1[O:33][C:34]2[C:40]([O:41][CH3:42])=[CH:39][CH:38]=[CH:37][C:35]=2[CH:36]=1)[OH:31])(C(C)(C)C)(C)C>>[CH3:42][O:41][C:40]1[C:34]2[O:33][C:32]([CH:30]([OH:31])[CH2:29][CH2:28][CH2:27][OH:26])=[CH:36][C:35]=2[CH:37]=[CH:38][CH:39]=1

Participants

3

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 184236524-(tert-Butyldimethylsilanyloxy)-1-(7-methoxybenzofuran-2-yl)-butan-1-ol

Product 1

HCID 184236471-(7-Methoxybenzofuran-2-yl)-butane-1,4-diolYield 86.8%

Procedure

Tetrabutylammonium fluoride (12 ml, 1M in tetrahydrofuran) was added to a stirred solution of 4-(tert-butyldimethylsilanyloxy)-1-(7-methoxybenzofuran-2-yl)-butan-1-ol (4 g) in tetrahdrofuran (50 ml) at 0° C. After stirring cooled for 2 hours the reaction was warmed to room temperature and allowed to stir for a further 1 hour. The solvent was removed in vacuo and the residue partitioned between ethyl acetate (100 ml) and water (50 ml). The organic extract was dried over magnesium sulphate, filtered and preadsorbed onto silica. Purification by column chromatography on silica eluting with ethyl acetate yielded the title compound as a tan oil (2.34 g).

Workup

  1. temperaturecooled for 2 hours the reaction
  2. stirringto stir for a further 1 hour
  3. customThe solvent was removed in vacuo
  4. customthe residue partitioned between ethyl acetate (100 ml) and water (50 ml)
  5. extractionThe organic extract
  6. dry with materialwas dried over magnesium sulphate
  7. filtrationfiltered
  8. customPurification by column chromatography on silica eluting with ethyl acetate

Sources & evidence

ORD record
ord-8cf74de0831b4279b132d992b099277d
Source dataset
uspto-grants-2001_12
Patent number
US06331556B2

Reaction notes

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