HCID 10634568, compound → HCID 21680573, compound

HRID 1955367Notes

Reaction equation

HRID 1955367 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:18])=[C:5]([CH2:11][CH:12]([CH3:17])[CH2:13][C:14]([OH:16])=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]>C(Cl)Cl>[CH3:1][O:2][C:3]1[C:4]([CH3:18])=[C:5]2[C:6](=[CH:7][C:8]=1[O:9][CH3:10])[C:14](=[O:16])[CH2:13][CH:12]([CH3:17])[CH2:11]2

Participants

3

Reactant 1

HCID 10634568HCID 10634568, compound

Product 1

HCID 21680573HCID 21680573, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 15a (7.0 g, 27.7 mmol) was added to 35 g of polyphosphoric ester in 100 mL of methylene chloride and refluxed for 1 h. The reaction mixture was poured onto ice, stirred to hydrolyze the polyphosphoric ester, and the resulting solid was filtered and recrystallized from methanol to give 5.4 g (23.0 mmol, 83% yield) of 16a as white plates: mp 106-108° C. 1H NMR:(ppm) 7.48 (s, 1H), 3.89 (s, 3H), 3.84 (s, 3H), 2.95-2.28 (mult, 5H), 2.22 (s, 3H), 1.18 (d, 3H). Anal. (C14H18O3) C,H.

Workup

  1. temperaturerefluxed for 1 h
  2. additionThe reaction mixture was poured onto ice
  3. filtrationthe resulting solid was filtered
  4. customrecrystallized from methanol

Sources & evidence

ORD record
ord-2f6852cae6a54126923a5b0d02326fd4
Source dataset
uspto-grants-2000_09
Patent number
US06124498

Reaction notes

Loading…