Methyl 3-formylbenzoate → HCID 67839300, compound

HRID 1109768Notes

Reaction equation

HRID 1109768 reaction equation
[Cl-].[F:2][C:3]1[CH:4]=[CH:5][C:6]2[S:10][C:9]([CH2:11][P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)=[N:8][C:7]=2[CH:31]=1.C([Li])CCC.[CH:37]([C:39]1[CH:40]=[C:41]([CH:46]=[CH:47][CH:48]=1)[C:42]([O:44][CH3:45])=[O:43])=O>CCCCCC.O1CCCC1>[F:2][C:3]1[CH:4]=[CH:5][C:6]2[S:10][C:9](/[CH:11]=[CH:37]/[C:39]3[CH:40]=[C:41]([CH:46]=[CH:47][CH:48]=3)[C:42]([O:44][CH3:45])=[O:43])=[N:8][C:7]=2[CH:31]=1

Participants

6

Reactant 3

HCID 639145Methyl 3-formylbenzoateHCID 19019462HCID 19019462, compoundHCID 178418339Butyllithium

Product 1

HCID 67839300HCID 67839300, compoundYield 76.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

Using the procedure of Preparation El and starting with 5.65 g of 5-fluorobenzothiazol-2-ylmethyl triphenyl phosphonium chloride (prepared by reacting 4.0 g of 2-chloromethyl-5-fluorobenzothiazole and 5.22 g of triphenylphosphine in 50 ml of toluene at reflux temperature for 17 hours), 7.61 ml of 1.6M n-butyl lithium solution in hexane and 2.0 g of methyl 3-formylbenzoate in 80 ml of dry tetrahydrofuran there was obtained 2.92 g of the titled product, m.p. 172°-173° C.

Workup

  1. customthe procedure of Preparation El

Sources & evidence

ORD record
ord-657766aafa3c47009d99c9495fa422c2
Source dataset
uspto-grants-1994_06
Patent number
US05322847

Reaction notes

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