Tetrahydrofuran → 4-(4-Isopropoxymethylbenzyl)-phenylamine

HRID 2121019Notes

Reaction equation

HRID 2121019 reaction equation
C[Si](C)(C)CCOC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][O:22][CH:23]([CH3:25])[CH3:24])=[CH:17][CH:16]=2)=[CH:10][CH:9]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>CS(C)=O>[CH:23]([O:22][CH2:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][C:11]2[CH:10]=[CH:9][C:8]([NH2:7])=[CH:13][CH:12]=2)=[CH:16][CH:17]=1)([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 691459544-(4-Isopropoxymethylbenzyl)phenyl carbamic acid 2-trimethylsilanylethyl ester

Product 1

HCID 218768564-(4-Isopropoxymethylbenzyl)-phenylamineYield 86.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 4-(4-isopropoxymethylbenzyl)phenyl carbamic acid 2-trimethylsilanyl-ethyl ester (734 mg, 1.84 mmol) in dry dimethyl sulfoxide at 20° C. under argon atmosphere was added tetra-n-butylammonium fluoride in tetrahydrofuran (5.52 mL, 5.52 mmol). After the mixture was stirred for 1 hour, the solution was partitioned between water (50 mL) and diethyl ether (50 mL). The aqueous phase was extracted with diethyl ether (2×20 mL), and the, combined organic layers were washed with water and brine, dried (Mg2SO4), and evaporated in vacuo. The crude product was purified by flash chromatography to give pure 4-(4-isopropoxymethyl-benzyl)-phenylamine (405 mg, 86%) as a clear oil.

Workup

  1. customthe solution was partitioned between water (50 mL) and diethyl ether (50 mL)
  2. extractionThe aqueous phase was extracted with diethyl ether (2×20 mL)
  3. washwere washed with water and brine
  4. dry with materialdried (Mg2SO4)
  5. customevaporated in vacuo
  6. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-70d9b452490348238e1a36258f2a6aca
Source dataset
uspto-grants-2004_02
Patent number
US06693200B2

Reaction notes

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