Triphenylphosphine → 1,4,7,10,13,16-Hexaoxacyclooctadecane-2,8,14-trione

HRID 468601Notes

Reaction equation

HRID 468601 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.ClCCl.C1(C)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.O[CH2:43][CH2:44][O:45][CH2:46][C:47](=[O:63])[O:48][CH2:49][CH2:50][O:51][CH2:52][C:53](=[O:62])[O:54][CH2:55][CH2:56][O:57][CH2:58][C:59]([OH:61])=[O:60]>C1(C)C=CC=CC=1>[O:60]1[CH2:43][CH2:44][O:45][CH2:46][C:47](=[O:63])[O:48][CH2:49][CH2:50][O:51][CH2:52][C:53](=[O:62])[O:54][CH2:55][CH2:56][O:57][CH2:58][C:59]1=[O:61]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 21877217Toluene methylene chlorideHCID 8667406017-Hydroxy-7,13-dioxo-3,6,9,12,15-pentaoxaheptadecan-1-oic acid

Product 1

HCID 866740591,4,7,10,13,16-Hexaoxacyclooctadecane-2,8,14-trioneYield 61.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of triphenylphosphine (4.68 g, 17.85 mmol) in a dichloromethane/toluene 1/1 mixture (1.5 l) was added at room temperature DEAD (8.2 ml, 44.63 mmol). Reaction mixture stirred at room temperature for 10 min then a toluene solution of hydroxyacid 12 (1.18 g, 3.57 mmol) was added. Mixture was stirred at room temperature and concentrated. Careful flash chromatography on silica gel (EtOAc/pentane 1/1 then 2/1 then EtOAc 100%) afforded cyclic 14 as a white solid (670 mg, 60%).

Workup

  1. customReaction mixture
  2. stirringMixture was stirred at room temperature
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9d654bc7f88647ac934c06beb80eb89f
Source dataset
uspto-grants-2014_01
Patent number
US08624044B2

Reaction notes

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