Acetyl chloride → HCID 19968564, compound

HRID 975922Notes

Reaction equation

HRID 975922 reaction equation
[CH3:1][O:2][C:3]1[C:4]([N+:20]([O-:22])=[O:21])=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](O[Si](C)(C)C)([C:13]#[N:14])[CH2:8][CH2:7][CH2:6]2.C(Cl)(C)=O>CC(O)=O>[CH3:1][O:2][C:3]1[C:4]([N+:20]([O-:22])=[O:21])=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([C:13]#[N:14])=[CH:8][CH2:7][CH2:6]2

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 19968569HCID 19968569, compound

Product 1

HCID 19968564HCID 19968564, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 6-methoxy-5-nitro-1-trimethylsilyloxy-l,2,3,4-tetrahydronaphthalene-1-carbonitrile (1.3 g, 4.0 mmol) and AcCl (1.0 ml) in 20 ml AcOH was stirred for 2 h at 80°-100° C. The resulting reaction mixture was concentrated in vacuo to yield the desired product as a colorless oil (0.86 g, 4.0 mmol, 96% for two steps), which was subjected to the following step without any further purification. 1H NMR (300 MHz, CDCl3):δ 2.48 (dt, 2H, J=2.3, 6.7 Hz), 2.78 (t, 2H, J=8.9 Hz ), 3.89 (s, 3H), 6.82 (t, 1H, J=2.3 Hz), 6.92 (d, 1H, J=8.9 Hz), 7.53 (d, 1H, J=8.9 Hz).

Workup

  1. customThe resulting reaction mixture
  2. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-5224029e966c4a99926e5c6e3d080c04
Source dataset
uspto-grants-1997_03
Patent number
US05610174

Reaction notes

Loading…