Diisopropylamine → HCID 86617051, compound

HRID 538724Notes

Reaction equation

HRID 538724 reaction equation
C(NC(C)C)(C)C.[C:8]([O:12][C:13](=[O:15])[CH3:14])([CH3:11])([CH3:10])[CH3:9].[O:16]([C:23]1[CH:33]=[CH:32][C:26]([C:27](OCC)=[O:28])=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[NH4+].[Cl-]>O1CCCC1>[O:28]=[C:27]([C:26]1[CH:32]=[CH:33][C:23]([O:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[CH:24][CH:25]=1)[CH2:14][C:13]([O:12][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:15]

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 10908tert-Butyl acetateHCID 25517Ammonium ChlorideHCID 5083196Ethyl 4-phenoxybenzoate

Product 1

HCID 86617051HCID 86617051, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

nButyllithium (2.5 M, 7.9 ml, 19.76 mmol) was added at −20° C. to a solution of di-iso-propylamine (3.29 ml, 23.24 mmol) in tetrahydrofuran (40 ml). The reaction mixture was stirred for 15 minutes under nitrogen at −20° C. then the mixture was allowed to cool down to −78° C. tert-Butylacetate (2.64 ml, 19.67 mmol) was added and the mixture was stirred at −78° C. for 20 minutes. A solution of ethyl 4-phenoxybenzoate (2.17 g, 8.94 mmol) in tetrahydrofuran (5 ml) was further added to this and the resulting mixture was stirred at −78° C. for 50 minutes. A saturated solution of NH4Cl was added and the whole was extracted with EtOAc. The organics were dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with 8% Et2O in petroleum ether to afford the title compound as a colourles oil (1.53 g, 55% yield). MS (ES+) m/e=313. 1H NMR (CDCl3) δH 1.47 (9H, s), 3.88 (2H, s), 7.02 (2H, d), 7.10 (2H, d), 7.24 (1H, t), 7.43 (2H, t), 7.94 (2H, d).

Workup

  1. additionwas added
  2. stirringthe mixture was stirred at −78° C. for 20 minutes
  3. stirringwas stirred at −78° C. for 50 minutes
  4. extractionthe whole was extracted with EtOAc
  5. dry with materialThe organics were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with 8% Et2O in petroleum ether

Sources & evidence

ORD record
ord-ad9469d9ffdb4fb8a53ccfeeb3007567
Source dataset
uspto-grants-2014_10
Patent number
US08865751B2

Reaction notes

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