TBAF tetrahydrofuran → HCID 59706557, compound

HRID 1774410Notes

Reaction equation

HRID 1774410 reaction equation
[Si]([O:8][C:9]1[CH:28]=[CH:27][C:12]([CH2:13]/[C:14](=[C:19](\[CH:24]([CH3:26])[CH3:25])/[C:20]([O:22][CH3:23])=[O:21])/[C:15]([O:17][CH3:18])=[O:16])=[CH:11][CH:10]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.CCCCCC.C(OCC)(=O)C>O1CCCC1>[CH3:18][O:17][C:15](=[O:16])/[C:14](/[CH2:13][C:12]1[CH:11]=[CH:10][C:9]([OH:8])=[CH:28][CH:27]=1)=[C:19](/[CH:24]([CH3:25])[CH3:26])\[C:20]([O:22][CH3:23])=[O:21]

Participants

5

Reactant 3

HCID 11078149TBAF tetrahydrofuranHCID 21226206Ethyl acetate hexaneHCID 66648815HCID 66648815, compound

Product 1

HCID 59706557HCID 59706557, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of dimethyl 2-[4-(t-butyldimethylsilyloxy)benzyl]-3-isopropylmaleate (823 mg, 2.02 mmol) in tetrahydrofuran (13 mL) was added a 1 M tetrabutylammonium fluoride-tetrahydrofuran solution (2.1 mL, 2.1 mmol) at room temperature, and the mixture was left standing at room temperature for 1 h. The reaction mixture was directly concentrated under reduced pressure and the residue thus obtained was subjected to silica gel column chromatography (hexane-ethyl acetate 2:1) to give 592 mg of 2-(4-hydroxybenzyl)-3-isopropylmaleic acid dimethyl ester as a solid (quantitative).

Workup

  1. waitthe mixture was left
  2. concentrationThe reaction mixture was directly concentrated under reduced pressure
  3. customthe residue thus obtained

Sources & evidence

ORD record
ord-844ee8f37aab44ee918366a3b5f42cd7
Source dataset
uspto-grants-2016_02
Patent number
US09260375B2

Reaction notes

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