Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | (Dimethyl sulfide)trihydroboron | HCID 12423031 | — |
| Reactant | HCID 53330278 | HCID 53330278 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 53330279 | HCID 53330279 | 85.3% |
Reaction Steps
To a solution of silyl ester 29 (38.0 g, 65.8 mmol) in THF (300 mL) was added borane dimethylsulfide complex (1 M in THF, 13 mL) at 0° C. The mixture was stirred 0° C. for 15 min, at room temperature at 30 min, and at 75° C. for 15 h. The mixture was cooled to 0° C. MeOH and H2O were added to the cooled mixture to quench the reaction. After dilution with water, the mixture was extracted with EtOAc. The organic layer was dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified by silica column chromatography to provide the titled compound 30 (22.9 g, 85%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08586550B2 |
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| Source dataset | uspto-grants-2013_11 |
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| ORD ID | ord-4342890cfc164c2693919815cb20cdc5 |
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| Source note | uspto-grants-2013_11 |
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