4-Toluenesulfonyl chloride → HCID 10965800, compound

HRID 639203Notes

Reaction equation

HRID 639203 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH2:8][CH2:7][CH2:6]2.C(NC(C)C)(C)C.[Li].C1(C)C=CC(S([Cl:31])(=O)=O)=CC=1>C1COCC1>[Cl:31][CH:8]1[CH2:7][CH2:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[C:9]1=[O:13]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 141126-Methoxy-alpha-tetraloneHCID 45051747Lithium diisopropylamine

Product 1

HCID 10965800HCID 10965800, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 6-Methoxy-3,4-dihydro-2H-naphthalen-1-one (5.0 g, 28.37 mmol) in THF (25 ml) is slowly added under an atmosphere of argon at −78° C. to a solution of lithium diisopropyl amine in THF (25 ml; prepared from 4.0 ml of diisopropylamine (28.37 mmol) and 17.7 ml of 1.6 M n-BuLi in hexane (28.37 mmol)). After 30 minutes at −78° C., a solution of para-tolylsulfonyl chloride (5.41 g, 28.37 mmol) in THF (25 ml) is added during 20 minutes. The dry ice cooling bath is removed, and the reaction mixture is allowed to reach RT. After 1 h, TLC analysis indicates complete consumption of starting material. A sat. aqueous solution of NH4Cl (100 ml) is added, and the mixture is stirred at RT for 15 minutes. The organic layer is separated, washed with brine, dried over Na2SO4 and concentrated. Purification by FCC (hexane/EtOAc 920:80 to 880:120) yields the title compound. 1H NMR (CDCl3, 400 MHz): δ 2.54-2.63 (m, 1H), 2.68-2.75 (m, 1H), 3.04-3.12 (m, 1H), 3.38-3.46 (m, 1H), 4.02 (s, 3H); 4.72-4.76 (m, 1H), 6.87 (s, 1H), 7.00-7.04 (m, 1H), 8.22 (d, J=10 Hz, 1H). ES+-MS: 279.1, 280.9 [M+H]+.

Workup

  1. customThe dry ice cooling bath is removed
  2. customto reach RT
  3. waitAfter 1 h
  4. customconsumption of starting material
  5. additionA sat. aqueous solution of NH4Cl (100 ml) is added
  6. customThe organic layer is separated
  7. washwashed with brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated
  10. customPurification by FCC (hexane/EtOAc 920:80 to 880:120)

Sources & evidence

ORD record
ord-d938fde65ac74c059c51e64f816095a9
Source dataset
uspto-grants-2010_04
Patent number
US07691861B2

Reaction notes

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