HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Acid → HCID 86679529, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Morpholine | HCID 8083 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | 2-(Benzyloxy)-2-oxoethyl 4-(cyclopropylmethoxy)-3-formylbenzoate | HCID 86679528 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 86679529 | HCID 86679529 | 100% |
Reaction Steps
A solution of 2-(benzyloxy)-2-oxoethyl 4-(cyclopropylmethoxy)-3-formylbenzoate (3.73 g, 10.13 mmol) and morpholine (1.15 g, 13.17 mmol) in dry THF (50 ml), under argon atmosphere, was stirred for 15 minutes at RT. Na(OAc)3BH (2.79 g, 13.17 mmol) and CH3COOH (754 μl, 13.17 mmol) were added. CH3COOH was added to reach a pH between 5 and 6. The mixture stirred at RT for 24 hours. The solvent was removed, and the crude was dissolved in EtOAc and washed with NaHCO3 sat. sol. and brine. The organic phase was dried over Na2SO4, and the solvent was removed to give 2-(benzyloxy)-2-oxoethyl 4-(cyclopropylmethoxy)-3-(morpholinomethyl)benzoate (4.45 g, quantitative yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09265768B2 |
| Source dataset | uspto-grants-2016_02 |
| ORD ID | ord-8f22cf2589b74c1693b6a7780c354d28 |
| Source note | uspto-grants-2016_02 |