Carbon Tetrachloride → HCID 57794780, compound

HRID 2099290Notes

Reaction equation

HRID 2099290 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Cl:24])(Cl)(Cl)Cl.[C:25]1([C@@:31]2(CO)[CH2:33][C@H:32]2[CH2:34][O:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(Cl)Cl>[Cl:24][CH2:20][C@:31]1([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:33][C@H:32]1[CH2:34][O:35][CH2:36][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 57794759HCID 57794759, compound

Product 1

HCID 57794780HCID 57794780, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of polymer-bound triphenylphosphine (31.64 g, 67.08 mmol, 3 eq) and carbon tetrachloride (6.5 mL, 67.08 mmol, 3 eq) in 300 mL DCM was stirred at ambient temperature for 30 min. To this was added a solution of ((1R,2R)-1-phenyl-2{[(phenylmethyl)oxy]methyl)cyclopropyl)methanol (6.0 g, 22.36 mmol, 1 eq), accessed via the method of Preparation 20B, in 50 mL DCM and the entire reaction mixture was stirred at ambient temperature for 16 h. The mixture was then filtered and the resin washed with excess DCM. The organics were concentrated down to give the title compound (6.4 g, 22.36 mmol, 100%) as a clear oil. 1H NMR (400 MHz, DMSO-d6) δ 7.38-7.17 (m, 10H), 4.31-4.16 (m, 2H), 4.10-4.07 (m, 1H), 3.56-3.53 (m, 1H), 3.08-3.04 (m, 1H), 2.92-2.87 (m, 1H), 1.63-1.56 (m, 1H), 1.08-0.99 (m, 2H).

Workup

  1. customthe entire reaction mixture
  2. stirringwas stirred at ambient temperature for 16 h
  3. filtrationThe mixture was then filtered
  4. washthe resin washed with excess DCM
  5. concentrationThe organics were concentrated down

Sources & evidence

ORD record
ord-dc05e64d63f84caebc6ff427c5d34fc3
Source dataset
uspto-grants-2009_08
Patent number
US07569579B2

Reaction notes

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