Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Isobutyraldehyde | HCID 6561 | — |
| Reactant | Boron trifluoride etherate | HCID 8000 | — |
| Reactant | 1,3-Propanedithiol | HCID 8013 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 637973 | HCID 637973 | 100% |
Reaction Steps
To a mixture of isobutyraldehyde (9.1 mL, 100 mmol) and 1,3-propanedithiol (10 mL, 100 mmol) in dichloromethane at 0° C. was added boron trifluoride diethyl etherate (6.4 mL, 50 mmol). The resulting mixture was stirred at 0° C. for 30 min and at room temperature for 30 min. The reaction mixture was washed with brine, 5% NaHCO3, and brine again. The organic phase was separated and dried over Na2SO4, then concentrated to give 16 g (100%) of the title compound as a yellow liquid. This was carried to the next step without further purification. 1H NMR (CDCl3, 400 MHz): δ 1.057 (d, J=7.2 Hz, 3H), 1.059 (d, J=7.2 Hz, 3H), 1.80 (m, 1H), 1.97-2.08 (m, 2H), 2.82 (m, 4H), 4.00 (d, J=5.2 Hz, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08168623B2 |
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| Source dataset | uspto-grants-2012_05 |
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| ORD ID | ord-312e8ab8c9a0435f95d59cc390cf182d |
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| Source note | uspto-grants-2012_05 |
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