Methyl 6-chlorohexanoate → Tetramethyl 5-methoxycarbonylpentyl-methanebisphosphonate

HRID 1950663Notes

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH3:10])=[O:8].[CH2:11]([P:18]([O:22][CH3:23])(=[O:21])[O:19][CH3:20])[P:12]([O:16][CH3:17])(=[O:15])[O:13][CH3:14]>>[CH3:10][O:9][C:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH:11]([P:12]([O:13][CH3:14])(=[O:15])[O:16][CH3:17])[P:18]([O:22][CH3:23])(=[O:21])[O:19][CH3:20])=[O:8]

Participants

Reactant 2

HCID 84311Methyl 6-chlorohexanoate

HCID 519206Tetramethyl methylenediphosphonate

Product 1

HCID 86594668Tetramethyl 5-methoxycarbonylpentyl-methanebisphosphonate

Procedure

Following the General Synthetic Procedure B, methyl 6-chlorohexanoate is reacted with tetramethyl methanebisphosphonate to produce tetramethyl 5-methoxycarbonylpentyl-methanebisphosphonate that is then hydrolyzed to yield 5-carboxypentyl-methanebisphosphonic acid, and then hydrogenated to reduce the carboxy group to a hydroxymethylene group. The resulting 6-hydroxyhexyl-methanebisphosphonic acid is then methacrylated with methacryloyl chloride to afford 6-methacryloxyhexyl-methanebisphosphonic acid.

Sources & evidence

ORD record: ord-58f620c6e9884a6a98fbea8a336f1355
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08404144B2

Reaction notes

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