Diisopropylamine → HCID 14223731, compound

HRID 477900Notes

Reaction equation

HRID 477900 reaction equation
C([N-][CH:5]([CH3:7])C)(C)C.[Li+].C(NC(C)C)(C)C.[CH2:16]([Li])[CH2:17][CH2:18][CH3:19].C[O:22][C:23]1[CH:28]=CC=C[C:24]=1[S:29](C)=[O:30].[O:32]1CCC[CH2:33]1>C(OCC)(=O)C>[CH3:33][O:32][C:16]1[CH:7]=[CH:5][C:19]([S:29]([CH2:24][C:23](=[O:22])[CH3:28])=[O:30])=[CH:18][CH:17]=1

Participants

7

Reactant 5

HCID 7912DiisopropylamineHCID 8028Tetrahydrofuran2×HCID 2724682Lithium diisopropylamideHCID 10979680Benzene, 1-methoxy-2-(methylsulfinyl)-HCID 178418339Butyllithium

Product 1

HCID 14223731HCID 14223731, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of lithium diisopropylamide prepared from diisopropylamine (27.3 g) and n-butyl lithium (161.75 ml, 1.6M) in tetrahydrofuran (700 ml), was added a solution of (-)-methyl methoxyphenyl sulfoxide (20 g) in tetrahydrofuran (40 ml) at -20° C. After 15 minutes, ethyl acetate (22.8 g) was added and the mixture was allowed to reach room temperature. After quenching with NaH2PO4, the solvent was removed in vacuo and the residue was extracted with ether. The extract was purified by chromatography on silica gel (1:1 acetone/hexane) to give (-)-4-methoxyphenylsulfinylacetone, m.p. 56°-58° C., [α]D =-149.8° (C=0.032, methanol).

Workup

  1. customto reach room temperature
  2. customAfter quenching with NaH2PO4
  3. customthe solvent was removed in vacuo
  4. extractionthe residue was extracted with ether
  5. customThe extract was purified by chromatography on silica gel (1:1 acetone/hexane)

Sources & evidence

ORD record
ord-b9dccd3e2fd14f5c9653f194865d0f4d
Source dataset
uspto-grants-1989_12
Patent number
US04889866

Reaction notes

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