Dimethylformamide → 3-Methoxy-5,5-dimethyl-6-oxo-5,6,7,8-tetrahydro-naphthalen-2-sulfonyl chloride

HRID 2275152Notes

Reaction equation

HRID 2275152 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=[O:15])[C:10]2([CH3:14])[CH3:13])=[CH:5][CH:4]=1.[Cl:16][S:17](O)(=[O:19])=[O:18].C(Cl)(=O)C(Cl)=O.CN(C)C=O>ClCCl>[CH3:1][O:2][C:3]1[C:4]([S:17]([Cl:16])(=[O:19])=[O:18])=[CH:5][C:6]2[CH2:7][CH2:8][C:9](=[O:15])[C:10]([CH3:13])([CH3:14])[C:11]=2[CH:12]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24638Chlorosulfonic acidHCID 65578Oxalyl chlorideHCID 130110077-Methoxy-1,1-dimethyl-3,4-dihydronaphthalen-2(1H)-one2×

Product 1

HCID 866638203-Methoxy-5,5-dimethyl-6-oxo-5,6,7,8-tetrahydro-naphthalen-2-sulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the dichloromethane (2 ml) solution of 7-methoxy-1,1-dimethyl-3,4-dihydro-1H-naphthalen-2-one (Compound A2, 200 mg, 0.980 mmol), chlorosulfonic acid (110 μl, 1.70 eq.) was added and the mixture was stirred at room temperature for 2 hr. To the reaction solution, oxalyl chloride (297 μl, 3.0 eq.) and N,N-dimethyl formamide (45 μl, 0.6 eq.) were added in three divided portions, and the mixture was stirred at room temperature for 30 min. The reaction solution was concentrated under reduced pressure to obtain the title compound (295 mg). Since the title compound is unstable, its structure was identified in the next step.

Workup

  1. stirringthe mixture was stirred at room temperature for 30 min
  2. concentrationThe reaction solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b6fc49a3012e405aa0eee9a3f2d381fc
Source dataset
uspto-grants-2015_09
Patent number
US09126931B2

Reaction notes

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