p-Toluenesulfonic acid → HCID 67171703, compound

HRID 1506562Notes

Reaction equation

HRID 1506562 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][C:8](=[O:13])[CH2:7][CH2:6]2.CO[CH:16](OC)[N:17]([CH3:19])[CH3:18].C1(C)C=CC(S(O)(=O)=O)=CC=1>>[CH3:16][N:17](/[CH:19]=[C:9]1/[C:8](=[O:13])[CH2:7][CH2:6][C:5]2[C:10]/1=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH3:18]

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 755826-Methoxy-1,2,3,4-tetrahydronaphthalen-2-oneHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 67171703HCID 67171703, compound

Procedure

6-methoxy-3,4-dihydronaphthalen-2(1H)-one (460 mg, 2.61 mmol) was dissolved in N,N-dimethylformamide dimethyl acetal (8 mL, 26.1 mmol) at room temperature. Within 5 minutes the solution had turned dark green in color. Next, p-toluenesulfonic acid (10 mg, 0.053 mmol) was added and the reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure and dried under vacuum to afford the title compound as a dark red oil. LC/MS M+1=232.2. The material was used for subsequent reactions without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customdried under vacuum

Sources & evidence

ORD record
ord-7f7a13d6a0004304811c6bd7b37d9d38
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

Loading…