Water → 5-Cyano-5-(diethoxy-phosphoryl)-4-(tetrahydro-pyran-4-yl)-pentanoic acid

HRID 502863Notes

Reaction equation

HRID 502863 reaction equation
[CH2:1]([O:3][P:4]([CH:9]([C:21]#[N:22])[CH:10]([CH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)[CH2:11][CH2:12][CH:13]=C)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].ClCCl.[O-:26][Mn](=O)(=O)=O.[K+].OS([O-])=O.[Na+].[OH2:37]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(O)(=O)C>[C:21]([CH:9]([P:4]([O:5][CH2:6][CH3:7])([O:3][CH2:1][CH3:2])=[O:8])[CH:10]([CH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)[CH2:11][CH2:12][C:13]([OH:26])=[O:37])#[N:22]

Participants

8

Reactant 5

HCID 962WaterHCID 6344DichloromethaneHCID 516875Potassium PermanganateHCID 23665763Sodium BisulfiteHCID 59428163[1-Cyano-2-(tetrahydro-pyran-4-yl)-hex-5-enyl]-phosphonic acid diethyl ester

Product 1

HCID 594281685-Cyano-5-(diethoxy-phosphoryl)-4-(tetrahydro-pyran-4-yl)-pentanoic acid

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 176Acetic AcidSolvent

Procedure

In a flask, [1-cyano-2-(tetrahydro-pyran-4-yl)-hex-5-enyl]-phosphonic acid diethyl ester (7.18 g, 21.6 mmol), dichloromethane (245 mL), acetic acid (70 mL), tetrabutylammonium bromide (490 mg), and water (210 mL) were combined and stirred at room temperature. KMnO4 (15.35 g, 97.2 mmol) was then added portionwise over the next 3 hours, and the reaction mixture was stirred overnight at room temperature. Solid NaHSO3 was added carefully until the reaction mixture became clear. The reaction mixture layers were separated, and the solvent was removed in vacuo to yield the title compound as a residue.

Workup

  1. stirringthe reaction mixture was stirred overnight at room temperature
  2. customThe reaction mixture layers were separated
  3. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-298f1659a1534ef1b2690ec844b811a7
Source dataset
uspto-grants-2010_08
Patent number
US07776882B2

Reaction notes

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