Tetrabutylammonium Fluoride → ethyl (S)(E)-2-{2-[2-(1,3-dihydro-6-ethyl-4-hydroxy-7-methyl-3-oxoisobenzofuran-5-yl)ethylidene]cyclopent-1-yl}acetate

HRID 1757215Notes

Reaction equation

HRID 1757215 reaction equation
[Si]([O:8][C:9]1[C:17]([CH2:18]/[CH:19]=[C:20]2/[C@H:21]([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:22][CH2:23][CH2:24]/2)=[C:16]([CH2:31][CH3:32])[C:15]([CH3:33])=[C:14]2[C:10]=1[C:11](=[O:34])[O:12][CH2:13]2)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH2:31]([C:16]1[C:15]([CH3:33])=[C:14]2[C:10]([C:11](=[O:34])[O:12][CH2:13]2)=[C:9]([OH:8])[C:17]=1[CH2:18]/[CH:19]=[C:20]1/[C@H:21]([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:22][CH2:23][CH2:24]/1)[CH3:32]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131719102ethyl (S)(E)-2-{2-[2-(4-t-butyldimethylsilyloxy-1,3-dihydro-6-ethyl-7-methyl-3-oxoisobenzofuran-5-yl)ethylidene]cyclopent-1-yl}acetate

Product 1

HCID 131719103ethyl (S)(E)-2-{2-[2-(1,3-dihydro-6-ethyl-4-hydroxy-7-methyl-3-oxoisobenzofuran-5-yl)ethylidene]cyclopent-1-yl}acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of ethyl (S)(E)-2-{2-[2-(4-t-butyldimethylsilyloxy-1,3-dihydro-6-ethyl-7-methyl-3-oxoisobenzofuran-5-yl)ethylidene]cyclopent-1-yl}acetate (1.24 g) in tetrahydrofuran (8 ml) was cooled to 0° C. and treated with 1M tetrabutylammonium fluoride in tetrahydrofuran (3 ml). After 5 minutes, the reaction mixture was poured into ice water and extracted with ethyl acetate. The extracts were dried, evaporated and the residue chromatographed on silica gel (20% ethyl acetate/hexane) to give ethyl (S)(E)-2-{2-[2-(1,3-dihydro-6-ethyl-4-hydroxy-7-methyl-3-oxoisobenzofuran-5-yl)ethylidene]cyclopent-1-yl}acetate, m.p. 95.0°-95.7° C.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe extracts were dried
  3. customevaporated
  4. customthe residue chromatographed on silica gel (20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-29bc708011244abebddd58046161e3ae
Source dataset
uspto-grants-1995_08
Patent number
US05444072

Reaction notes

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