Sodium hydride → HCID 91207794, compound

HRID 1182448Notes

Reaction equation

HRID 1182448 reaction equation
[H-].[Na+].[CH3:3][O:4][CH:5]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[CH2:6][CH:7]=[CH:8][CH:9]=[CH:10][C:11](O)=[O:12].C(Cl)(=O)C([Cl:25])=O>C1C=CC=CC=1>[CH3:3][O:4][CH:5]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[CH2:6][CH:7]=[CH:8][CH:9]=[CH:10][C:11]([Cl:25])=[O:12]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 65578Oxalyl chlorideHCID 740152587-Methoxy-7-(4-methoxyphenyl)-2,4-heptadienoic acid

Product 1

HCID 91207794HCID 91207794, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a suspension of 60% NaH (0.059 g, 1.47 mmol) washed previously with dry pentane (2×5 mL) in dry benzene (5 mL) at 5° C. was added dropwise a solution of carboxylic acid 4 (0.30 g, 1.14 mmol) in dry benzene (5 mL) via cannula. After 20 min, oxalyl chloride (117 μL, 1.34 mmol) was added via microsyringe, and then the reaction mixture was allowed to warm to rt over 30 min. After stirring for an additional 1.5 h at rt, the mixture was filtered and the filtrate was concentrated under reduced pressure to give the desired acid chloride 5 in 93% yield as a red-orange oil. Without further purification, this crude product was used in the next step: 1H NMR (300 MHz, CDCl3) δ 7.40 (dd, J=15.3, 10.5 Hz, 1H), 7.20 (d, J=8.4 Hz, 2H), 6.90 (d, J=8.4 Hz, 2H), 6.30 (m, 2H), 5.98 (d, J=15.3 Hz, 1H), 4.18 (dd, J=7.5, 4.8 Hz, 1H), 3.82 (s, 3H ), 3.20 (s, 3H ), 2.61 (m, 1H), 2.48 (m, 1H).

Workup

  1. washwashed previously with dry pentane (2×5 mL) in dry benzene (5 mL) at 5° C.
  2. filtrationthe mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5d53356568ea4665923291690b0b8bee
Source dataset
uspto-grants-2007_10
Patent number
US07288567B2

Reaction notes

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