4-Toluenesulfonyl chloride → HCID 12962990, compound

HRID 1968716Notes

Reaction equation

HRID 1968716 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH2:9][C:10]2=[O:13])=[CH:5][CH:4]=1.C(NC(C)C)(C)C.[Li].C1(C)C=CC(S([Cl:31])(=O)=O)=CC=1>C1COCC1>[Cl:31][CH:9]1[CH2:8][CH2:7][C:6]2[C:11](=[CH:12][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:10]1=[O:13]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 812767-Methoxy-1,2,3,4-tetrahydronaphthalen-1-oneHCID 45051747Lithium diisopropylamine

Product 1

HCID 12962990HCID 12962990, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 7-Methoxy-3,4-dihydro-2H-naphthalen-1-one (25.6 g, 145.28 mmol) in THF (300 ml) is slowly added under an atmosphere of argon at −78° C. to a solution of lithium diisopropyl amine in THF (300 ml; prepared from 22.6 ml of diisopropylamine (160 mmol) and 100 ml of 1.6 M n-BuLi in hexane (160 mmol)). After 30 minutes at −78° C., a solution of para-tolylsulfonyl chloride (30.5 g, 159.8 mmol) in THF (300 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 3:1) yields the title compound. 1H NMR (CDCl3, 400 MHz): δ 2.32-2.52 (m, 2H), 2.82-2.90 (m, 2H), 3.10-3.18 (m, 2H), 3.78 (s, 1H), 4.52-4.58 (m, 1H), 7.01-7.05 (m, 1H), 7.11 (d, J=8.8 Hz, 1H), 7.47-7.48 (m, 1H). ES+-MS: 211.3, 213.3 [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 3:1)

Sources & evidence

ORD record
ord-712a24c303564a439738f1ffd29da8b9
Source dataset
uspto-grants-2013_04
Patent number
US08426440B2

Reaction notes

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