Triphenylphosphine → Methyl 3-((s)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-5-[(phenylmethyl)oxy]benzoate

HRID 548649Notes

Reaction equation

HRID 548649 reaction equation
[Si:1]([O:8][CH2:9][C@H:10]([OH:12])[CH3:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].O[C:14]1[CH:15]=[C:16]([CH:21]=[C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:23]=1)[C:17]([O:19][CH3:20])=[O:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Si:1]([O:8][CH2:9][C@H:10]([CH3:11])[O:12][C:14]1[CH:15]=[C:16]([CH:21]=[C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:23]=1)[C:17]([O:19][CH3:20])=[O:18])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 7472028Methyl 3-(benzyloxy)-5-hydroxybenzoateHCID 13175135(2R)-1-{[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}propan-2-ol

Product 1

HCID 59127165Methyl 3-((s)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-5-[(phenylmethyl)oxy]benzoateYield 80.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(2R)-1-{[tert-Butyl(dimethyl)silyl]oxy}propan-2-ol (3.31 g, 17.4 mmol) was added to a solution of methyl 3-hydroxy-5-{[phenylmethyl]oxy}benzoate (3.00 g, 11.6 mmol) in THF (50 mL) at 0° C. followed by addition of triphenylphosphine (4.57 g, 17.4 mmol) then DIAD (3.43 mL, 17.4 mmol) and the reaction was warmed to RT and stirred for 16 h. The reaction was quenched with water (100 mL) and diethyl ether (400 mL) and the organic layer was separated then dried (MgSO4) and evaporated. Purification by column chromatography, eluting with 1:15 to 1:5 ethyl acetate:hexane, afforded the title compound as a colourless oil (4.00 g, 80%).

Workup

  1. customThe reaction was quenched with water (100 mL) and diethyl ether (400 mL)
  2. customthe organic layer was separated
  3. dry with materialthen dried (MgSO4)
  4. customevaporated
  5. customPurification by column chromatography
  6. washeluting with 1:15 to 1:5 ethyl acetate

Sources & evidence

ORD record
ord-6c09c16c14d240e3992fd5586d683d31
Source dataset
uspto-grants-2011_05
Patent number
US07943607B2

Reaction notes

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