Triphenylphosphine → Methyl 3-(benzyloxy)-5-[(1S)-2-methoxy-1-methylethoxy]benzoate

HRID 20500Notes

Reaction equation

HRID 20500 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:39][O:40][CH2:41][C@H:42](O)[CH3:43].CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH3:39][O:40][CH2:41][C@@H:42]([O:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])[CH3:43]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 2733589(R)-(-)-1-Methoxy-2-propanolHCID 5363146Diisopropyl azodicarboxylateHCID 7472028Methyl 3-(benzyloxy)-5-hydroxybenzoate

Product 1

HCID 59127167Methyl 3-(benzyloxy)-5-[(1S)-2-methoxy-1-methylethoxy]benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-hydroxy-5-{[phenylmethyl]oxy}benzoate (77.4 mmol) in THF was added polymer-supported triphenylphosphine (51.7 g of 3 mmol/g loading, 155 mmol) and (R)-(−)-1-methoxy-2-propanol (102 mmol). The stirred solution was blanketed with argon and cooled in an ice bath. A solution of DIAD (116 mmol) was added dropwise by syringe over 10 minutes. The solution was stirred for 20 minutes and filtered, washing the residue with THF (500 mL). The filtrate and washings were combined, and evaporated to give the desired compound which was used without further purification.

Workup

  1. temperaturecooled in an ice bath
  2. filtrationfiltered
  3. washwashing the residue with THF (500 mL)
  4. customevaporated

Sources & evidence

ORD record
ord-f9de1b9e97054b5aaabc4d4e3ea7f6bd
Source dataset
uspto-grants-2010_06
Patent number
US07745475B2

Reaction notes

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