Sodium hydride → HCID 10086171, compound

HRID 488135Notes

Reaction equation

[H-].[Na+].CC[O:5][C:6]([CH:8](P(OCC)(OCC)=O)[CH3:9])=[O:7].[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:37]=O)[C:23]2[C:28]([C:29]=1[O:30]COC)=[C:27]([CH2:34][CH2:35][CH3:36])[CH:26]=[CH:25][CH:24]=2>CN(C)C=O.[Cl-].[Na+].O>[OH:30][C:29]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][C:27]=2[CH2:34][CH2:35][CH3:36])[C:22](/[CH:37]=[C:8](\[CH3:9])/[C:6]([OH:5])=[O:7])=[CH:21][C:20]=1[O:19][CH3:18]

Participants

Conditions

Temperature: 10 °C

Procedure

45 g of 60% sodium hydride was suspended in 650 ml of N,N-dimethylformamide and cooled to 10° C. 355 g of triethyl 2-phosphonopropionate was added to the solution to make a clear solution. A solution of 270 g of 3-methoxy-4-methoxymethoxy-5-propyl-1-naphthalenecarbaldehyde in N,N-dimethylformamide (250 ml) was dropped in the solution and stirred at room temperature for 1 hour. The reaction mixture was poured into brine and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (8% ethyl acetate/hexane) to obtain 325.3 g of the titled compound as a pale yellow oil (containing a small amount of Z isomer).

Workup

extractionextracted with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by silica gel column chromatography (8% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-cafc16cc7bc04f288156a8d71e2cb05d
Source dataset: uspto-grants-1994_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05298649

Reaction notes

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