Tetrabutylammonium Fluoride Trihydrate → HCID 86749281, compound

HRID 1781567Notes

Reaction equation

HRID 1781567 reaction equation
[Si]([O:8][C:9]1[C:17]([CH2:18]/[CH:19]=[C:20](\[CH3:32])/[CH:21]([CH2:28][CH2:29][CH2:30][Br:31])[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:16]([O:33][CH3:34])[C:15]([CH3:35])=[C:14]2[C:10]=1[C:11](=[O:36])[O:12][CH2:13]2)(C(C)(C)C)(C)C.O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.CCOCC>[OH:8][C:9]1[C:17]([CH2:18]/[CH:19]=[C:20](\[CH3:32])/[CH:21]([CH2:28][CH2:29][CH2:30][Br:31])[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:16]([O:33][CH3:34])[C:15]([CH3:35])=[C:14]2[C:10]=1[C:11](=[O:36])[O:12][CH2:13]2

Participants

5

Reactant 2

HCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 131719275HCID 131719275, compound

Product 1

HCID 86749281HCID 86749281, compoundYield 62.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of of ethyl (E) 6-(4-tert-butyldimethylsilyloxy -1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl) -3-(3-bromopropyl)-4-methylhex-4-enoate (1.62 g) was dissolved in THF (25 ml), cooled to 0° C., and a solution of tetrabutylammonium fluoride trihydrate (919 mg) in THF (5 ml) was added. The reaction was stirred for 15 min, diluted with ether, washed water (2×), brine, and dried. The solvent was evaporated, and the resulting oil chromatographed on silica gel (15%-20% ethyl acetate in hexanes) to give ethyl (E) 6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl -3-oxoisobenzofuran -5-yl)-3-(3-bromopropyl)-4-methylhex -4-enoate (810 mg ) .

Workup

  1. washwashed water (2×), brine
  2. customdried
  3. customThe solvent was evaporated
  4. customthe resulting oil chromatographed on silica gel (15%-20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-0320830997a041e49aaec6fb21a36af9
Source dataset
uspto-grants-1997_05
Patent number
US05633279

Reaction notes

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