Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Guaiacol | HCID 460 | — |
| Reactant | Phenol | HCID 996 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Diethyl azodicarboxylate | HCID 5462977 | — |
| Reactant | HCID 68960823 | HCID 68960823 | — |
| Catalyst | Palladium | HCID 23938 | — |
| Product | HCID 68966264 | HCID 68966264 | 80.5% |
Reaction Steps
Treatment of (±)-1-[2-(benzyloxy)-3-methoxyphenyl]-3-{[tert-butyl(dimethyl)silyl]oxy}propan-2-ol (58.14 g, 0.144 mol) with palladium on carbon (5.81 g, 10 wt. %) generally according to the procedure described for Intermediate 4 provided (±)-2-(3-[tert-butyl(dimethyl)silyl]oxy}-2-hydroxypropyl)-6-methoxyphenol as a crude oil. Treatment of the phenol with triphenylphosphine (44.52 g, 0.170 mol) and diethylazodicarboxylate (29.56 g, 0.170 mol) generally according to the procedure described for Intermediate 5 gave 34.12 g (80%) of (±)-tert-butyl[(7-methoxy-2,3-dihydro-1-benzofuran-2-yl)methoxy]dimethylsilane as a colorless oil. Rf=0.67 (silica, ethyl acetate:hexanes 1:9); Anal. calcd. for C16H26O3Si: C, 65.26; H, 8.90. Found: C, 64.26; H, 9.24.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07435837B2 |
|---|
| Source dataset | uspto-grants-2008_10 |
|---|
| ORD ID | ord-3f88fa8e47e943378c179e83d1f8aa0e |
|---|
| Source note | uspto-grants-2008_10 |
|---|
