Pyridine → Methyl 4-triphenylmethyloxy-3-hydroxybutyrate

HRID 1594448Notes

Reaction equation

[OH:1][CH:2]([CH2:8][OH:9])[CH2:3][C:4]([O:6][CH3:7])=[O:5].C(Cl)Cl.N1C=CC=CC=1.[C:19](Cl)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O>[C:20]1([C:19]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[O:9][CH2:8][CH:2]([OH:1])[CH2:3][C:4]([O:6][CH3:7])=[O:5])[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To 25 g of methyl 3,4-dihydroxybutanoate was added 250 mL of DCM and stirred to dissolve. 19.8 g of pyridine was added and cooled to 0° C. 41.4 g of trityl chloride was dissolved in 50 mL of DMC and was added at 0-5° C. for 15 minutes. The temperature was allowed to rise to room temperature and was stirred at room temperature for 17 hours. Water was added and the layers were separated. The organic layer was washed with brine, dried and concentrated. The residue was triturated with 25 mL of cyclohexane and the product was purified to give 15 g of the pure product. 1H NMR (CDCl3): 4.25 (m, 1H), 3.6 (s, 3H), 3.15 (d, 2H), 2.5 (m, 2H), 7.2-7.4 (m, 15H).

Workup

dissolutionto dissolve
additionwas added at 0-5° C. for 15 minutes
customto rise to room temperature
stirringwas stirred at room temperature for 17 hours
customthe layers were separated
washThe organic layer was washed with brine
customdried
concentrationconcentrated
customThe residue was triturated with 25 mL of cyclohexane
customthe product was purified

Sources & evidence

ORD record: ord-aebd074fa0174b8eb8f45f0d9731dd14
Source dataset: uspto-grants-2007_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07301046B2

Reaction notes

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