Triphenylphosphine → Methyl 2-(4-{2-[4-(methoxymethyl)phenyl]ethoxy}benzyl)butanoate

HRID 987139Notes

Reaction equation

HRID 987139 reaction equation
C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:38][O:39][CH2:40][C:41]1[CH:46]=[CH:45][C:44]([CH2:47][CH2:48][OH:49])=[CH:43][CH:42]=1.O[C:51]1[CH:64]=[CH:63][C:54]([CH2:55][CH:56]([CH2:61][CH3:62])[C:57]([O:59][CH3:60])=[O:58])=[CH:53][CH:52]=1>ClCCl.C(OCC)(=O)C>[CH3:38][O:39][CH2:40][C:41]1[CH:46]=[CH:45][C:44]([CH2:47][CH2:48][O:49][C:51]2[CH:64]=[CH:63][C:54]([CH2:55][CH:56]([CH2:61][CH3:62])[C:57]([O:59][CH3:60])=[O:58])=[CH:53][CH:52]=2)=[CH:43][CH:42]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 229884104-(Methoxymethyl)phenethyl alcoholHCID 22988421Methyl 2-(4-hydroxybenzyl)butanoate

Product 1

HCID 22988461Methyl 2-(4-{2-[4-(methoxymethyl)phenyl]ethoxy}benzyl)butanoateYield 60%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

ADDP (1,23 g, 4,89 mmole) and triphenylphosphine (1,03 g, 3,92 mmole) were added to a solution of 2-[4-(methoxymethyl)phenyl]ethanol (0,54 g, 3,26 mmole) and methyl 2-(4-hydroxybenzyl)butanoate (0,68 g, 3,26 mmole) in dry dichloromethane (10 ml) under argon. After 5 minutes, more dichloromethane (10 ml) was added. The reaction mixture was stirred at room temperature for 5.5 hours and then filtered. Purification by chromatography on silica gel using heptan:ethyl acetate (1:1) as eluent gave a mixture of product and starting material wich was dissolved in ethyl acetate and washed 3 times with 1 N sodium hydroxide. The organic phase was washed with brine, dried (sodium sulphate), filtered and solvent was evaporated to give 0,27 g (yield 60%) of the desired product.

Workup

  1. filtrationfiltered
  2. customPurification by chromatography on silica gel
  3. customgave
  4. additiona mixture of product
  5. washwashed 3 times with 1 N sodium hydroxide
  6. washThe organic phase was washed with brine
  7. dry with materialdried (sodium sulphate)
  8. filtrationfiltered
  9. customsolvent was evaporated

Sources & evidence

ORD record
ord-4102b13da38e48cfb173205a824373d4
Source dataset
uspto-grants-2003_10
Patent number
US06630509B2

Reaction notes

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