Ammonium Chloride → Methyl (E)-8-(2-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-6-hydroxy-7-octenoate

HRID 2243293Notes

Reaction equation

[BH4-].[Na+].[Si:3]([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1/[CH:17]=[CH:18]/[C:19](=[O:28])[CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4].[NH4+].[Cl-]>CO>[Si:3]([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1/[CH:17]=[CH:18]/[CH:19]([OH:28])[CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])([C:6]([CH3:7])([CH3:9])[CH3:8])([CH3:5])[CH3:4]

Participants

Conditions

Temperature: 0 °C

Procedure

At 0° C., 0.146 g (3.86 mmol) of sodium borohydride was added to a solution of 1.436 g (3.86 mmol) of CeCl3.7H2O and 3.67 mmol of methyl (E)-8-(2-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-6-oxo-7-octenoate from Ex. XIIc in 30 ml of methanol. The mixture was stirred at 0° C. and the progress of the reaction was monitored by thin-layer chromatography. Saturated NH4Cl solution was added, the mixture was extracted with ethyl acetate and the combined organic phases were dried over Na2SO4. The product was purified chromatographically (silica gel, cyclohexane/EA 10:2). This gave 1.38 g (91.5%) of a colorless liquid.

Workup

extractionthe mixture was extracted with ethyl acetate
dry with materialthe combined organic phases were dried over Na2SO4
customThe product was purified chromatographically (silica gel, cyclohexane/EA 10:2)

Sources & evidence

ORD record: ord-f5132f2afa3d4d319522aad048a5c249
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07674825B2

Reaction notes

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