Carbon Tetrachloride → HCID 13934490, compound

HRID 1030037Notes

Reaction equation

HRID 1030037 reaction equation
O[CH:2]1[CH2:6][CH2:5][C:4]([P:17]([O:23]C(C)C)(=[O:22])[O:18]C(C)C)([P:7]([O:13]C(C)C)(=[O:12])[O:8]C(C)C)[CH2:3]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:47]>>[Cl:47][CH:2]1[CH2:6][CH2:5][C:4]([P:17]([OH:23])(=[O:22])[OH:18])([P:7]([OH:13])(=[O:12])[OH:8])[CH2:3]1

Participants

4

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 15067931HCID 15067931, compound

Product 1

HCID 13934490HCID 13934490, compoundYield 69%

Procedure

Tetraisopropyl 3-hydroxycyclopentane-1,1-diphosphonate (3.00 g, 7.24 mmol) was dissolved in 50 mL dry CCl4. Triphenylphosphine (3.80 g, 14.5 mmol) was added and the mixture was refluxed for 72 h. The mixture was filtered, concentrated, and the residue chromatographed (3:2 hexane:THF) on silica gel to afford 2.15 g (69%) of the desired product as a clear, viscous oil: 1H NMR (CDCl3) chemical shift 4.97-4.68 (m, 4H, OCHMe2), 4.24 (m, 1H, J=7 Hz, CHOH), 2.65-1.87 (m, 6H, ring CH2), 1.36 (d, 24H, J=6 Hz, CH3); 31P NMR (CDCl3) 25.3, 24.9, 24.4, 24.0; ammonia Cl mass spectrum m/e 433, 435 (MH+).

Workup

  1. temperaturethe mixture was refluxed for 72 h
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated
  4. customthe residue chromatographed (3:2 hexane:THF) on silica gel

Sources & evidence

ORD record
ord-131b28e080e24cc19c81846a643a1381
Source dataset
uspto-grants-1992_04
Patent number
US05104863

Reaction notes

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