Nitrogen → HCID 58052550, compound

HRID 2190188Notes

Reaction equation

HRID 2190188 reaction equation
[CH2:1]([O:4][CH2:5][C:6]([CH3:12])([CH3:11])[C:7]([O:9][CH3:10])=[O:8])[CH:2]=C.[O:13]=[O+][O-].N#N.[BH4-].[Na+].[NH4+].[Cl-]>N1C=CC=CC=1.C(Cl)Cl.CO>[OH:13][CH2:2][CH2:1][O:4][CH2:5][C:6]([CH3:12])([CH3:11])[C:7]([O:9][CH3:10])=[O:8]

Participants

9

Reactant 5

HCID 947NitrogenHCID 24823OzoneHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 58052503HCID 58052503, compound

Product 1

HCID 58052550HCID 58052550, compoundYield 31%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

A mixture of crude methyl 3-(allyloxy)-2,2-dimethylpropanoate (7.28 g, 1 eq.), MeOH (63 ml), DCM (63 ml) and pyridine (16 ml) was cooled to −78° C. O3 was passed through the reaction mixture until the colorless solution turned light blue. N2 was passed for 1 min. NaBH4 (4.00 g, 2.5 eq.) was added. The reaction mixture was stirred at 0° C. for 3 h. Saturated aqueous NH4Cl was carefully added. The resulting mixture was extracted with EtOAc, dried over MgSO4 and concentrated. Silica gel chromatography using 6-66% EtOAc-heptane yields the title compound as a colorless oil (7.45 g, 31%).

Workup

  1. extractionThe resulting mixture was extracted with EtOAc
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-88be85aa82a347d6ad6a11993af67c78
Source dataset
uspto-grants-2012_12
Patent number
US08324239B2

Reaction notes

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