Oxalyl chloride → HCID 9869618, compound

HRID 382902Notes

Reaction equation

HRID 382902 reaction equation
C(Cl)(=O)C(Cl)=O.[Br:7][C:8]1[CH:9]=[C:10](/[C:15](/[CH3:25])=[CH:16]\[CH:17]=[CH:18]\[C:19](\[CH3:24])=[CH:20]\[C:21]([OH:23])=O)[CH:11]=[C:12]([Br:14])[CH:13]=1.C[Si](C)(C)[O:28][C:29]1[CH:34]=[CH:33][C:32]([NH:35][Si](C)(C)C)=[CH:31][CH:30]=1.[F-].[K+]>CN(C=O)C.CCOCC>[OH:28][C:29]1[CH:34]=[CH:33][C:32]([NH:35][C:21](=[O:23])/[CH:20]=[C:19](\[CH3:24])/[CH:18]=[CH:17]/[CH:16]=[C:15](\[C:10]2[CH:11]=[C:12]([Br:14])[CH:13]=[C:8]([Br:7])[CH:9]=2)/[CH3:25])=[CH:31][CH:30]=1

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 522689Potassium FluorideHCID 617129Silanamine, 1,1,1-trimethyl-N-[4-[(trimethylsilyl)oxy]phenyl]-HCID 86757555HCID 86757555, compound

Product 1

HCID 9869618HCID 9869618, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of dry ether (30 mL) and DMF (0.5 g, 7 mmol) was cooled to 15° C. and then treated with oxalyl chloride (0.2 g, 1.5 mmol) and stirred for 15 min. All solvent was then removed and dimethylchloroformamidinium chloride (Helv. Chim. Acta 42, 1653 (1959)) as a white solid was suspended in DMF (5 mL). To this was added (2E,4E,6Z)-7-(3,5-dibromophenyl)-3,7-dimethyl-2,4,6-heptatrienoic acid (0.30 g, 0.8 mmol) and the mixture was stirred at room temperature for 3-4 h. The reaction was cooled to 0° C. and treated over a 10 min period with a solution of O,N-bis(trimethylsilyl)-4-aminophenol (0.6 g, 2.4 mmol) in DMF (5 mL). Once the addition was complete stirring was continued for 1 h and then it was poured into 5% aqueous KF (10 mL) and stirred a further 1 h. The aqueous mixture was extracted with ether, purified by HPLC using 35% EtOAc/hexanes as eluent to give N-(4-hydroxyphenyl)-(2E,4E,6Z)-7-(3,5-dibromophenyl)-3,7-dimethyl-2,4,6-heptatrienamide.

Workup

  1. customAll solvent was then removed
  2. stirringthe mixture was stirred at room temperature for 3-4 h
  3. additionOnce the addition
  4. stirringwas complete stirring
  5. waitwas continued for 1 h
  6. stirringstirred a further 1 h
  7. extractionThe aqueous mixture was extracted with ether
  8. custompurified by HPLC

Sources & evidence

ORD record
ord-3b0ed56bb0104da8813ba670ed902944
Source dataset
uspto-grants-2001_10
Patent number
US06310247B1

Reaction notes

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