Tetrabutylammonium Fluoride Trihydrate → HCID 86749281, compound

HRID 2396653Notes

Reaction equation

HRID 2396653 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 (2X), 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-methoxy7-methyl-3-oxoisobenzofuran-5-yl)-3-(3-bromopropyl)-4-methylhex-4-enoate (810 mg).

Workup

  1. washwashed water (2X), 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-3b9432a5b5284bc78ab16fc9aba3df22
Source dataset
uspto-grants-1996_02
Patent number
US05493030

Reaction notes

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