Tetrabutylammonium Fluoride → 3,4-Dihydro-5-hydroxy-2,2,4-trimethyl-7-pentyl-2H-1-benzopyran-3-propanoic acid

HRID 399163Notes

Reaction equation

HRID 399163 reaction equation
CC([Si](C1C=CC=CC=1)(C1C=CC=CC=1)[O:6][C:7]1[C:12]2[CH:13]([CH3:24])[CH:14]([CH2:19][CH2:20][C:21]([OH:23])=[O:22])[C:15]([CH3:18])([CH3:17])[O:16][C:11]=2[CH:10]=[C:9]([CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH:8]=1)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:6][C:7]1[C:12]2[CH:13]([CH3:24])[CH:14]([CH2:19][CH2:20][C:21]([OH:23])=[O:22])[C:15]([CH3:18])([CH3:17])[O:16][C:11]=2[CH:10]=[C:9]([CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH:8]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 189701375-[[(1,1-Dimethylethyl)-diphenylsilyl]oxy]-3,4-dihydro-2,2,4-trimethyl-7-pentyl-2H-1-benzopyran-3-propanoic acid

Product 1

HCID 189701453,4-Dihydro-5-hydroxy-2,2,4-trimethyl-7-pentyl-2H-1-benzopyran-3-propanoic acidYield 67.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.0 g (1.75 mmol) of 5-[[(1,1-Dimethylethyl)-diphenylsilyl]oxy]-3,4-dihydro-2,2,4-trimethyl-7-pentyl-2H-1-benzopyran-3-propanoic acid in anhy. THF under argon was treated with 2.09 mL (2.09 mmol) of a 1M solution of tetrabutylammonium fluoride in THF (Aldrich). After stirring at RT for 1 hr the reaction was evaporated under reduced pressure and the residue subjected to column chromatography on flash-grade silica gel, eluting with 5% MeOH-CHCl3. The fractions containing product were combined and evaporated under reduced pressure to give 395 mg (67%) of 3,4-Dihydro-5-hydroxy-2,2,4-trimethyl-7-pentyl-2H-1-benzopyran-3-propanoic acid as a tan-colored foam. MA: Calc for C20H30 O4.0.2H2O: C, 71.06; H, 9.06; O, 19.29. Found: C, 70.93; H, 8.95; O, 19.27.

Workup

  1. customwas evaporated under reduced pressure
  2. washeluting with 5% MeOH-CHCl3
  3. additionThe fractions containing product
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-42a2738707d84588a403fd0ca9127e3b
Source dataset
uspto-grants-1998_10
Patent number
US05817766

Reaction notes

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