Carbon Tetrachloride → HCID 13934490, compound

HRID 1789163Notes

Reaction equation

HRID 1789163 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-a90e758761144eef9e5aad94c40127f7
Source dataset
uspto-grants-1987_08
Patent number
US04687768

Reaction notes

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