HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanol → 5-Bromo-2-methyl-2-phenylpentan-1-ol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Lithium borohydride | HCID 4148881 | — |
| Reactant | 6-Bromo-2-methyl-2-p-tolylhexan-1-ol | HCID 11196892 | — |
| Reactant | Ethyl 5-bromo-2-methyl-2-phenyl-pentanoate | HCID 23431358 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 5-Bromo-2-methyl-2-phenylpentan-1-ol | HCID 11345892 | 98.2% |
Reaction Steps
According to the procedure given for the synthesis of 206e, 205b (23.70 g, 79.21 mmol) was reduced with LiBH4 (3.45 g, 158.4 mmol) and methanol (5.24 g, 163.5 mmol) in anhydrous CH2Cl2 (150 mL) to give 206b (20.0 g, 98%) as an oil. 1H NMR (CDCl3): δ 7.34-7.14 (m, 5H), 3.60 (m, 1H), 3.48 (m, 1H), 3.29 (t, 2H, J=6.0), 1.96-1.44 (m, 5H), 1.32 (s, 3H). 13C NMR (CDCl3): δ 144.25, 128.59, 126.71, 126.41, 72.44, 43.15, 37.06, 34.64, 27.58, 21.61. HRMS (LSIMS, nba): Calcd for C12H16Br (MH+—H2O): 239.0435, found: 239.0444.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07705177B2 |
| Source dataset | uspto-grants-2010_04 |
| ORD ID | ord-b4394b114ac946948ec979a515e31546 |
| Source note | uspto-grants-2010_04 |