Guaiacol → HCID 68966264, compound

HRID 2115937Notes

Reaction equation

HRID 2115937 reaction equation
C(O[C:9]1[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:17][CH:18]([OH:28])[CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])C1C=CC=CC=1.COC1C(O)=CC=CC=1.C1(O)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>[Pd]>[C:24]([Si:21]([O:20][CH2:19][CH:18]1[CH2:17][C:10]2[CH:11]=[CH:12][CH:13]=[C:14]([O:15][CH3:16])[C:9]=2[O:28]1)([CH3:22])[CH3:23])([CH3:25])([CH3:26])[CH3:27]

Participants

7

Reactant 5

HCID 460GuaiacolHCID 996PhenolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 68960823HCID 68960823, compound

Product 1

HCID 68966264HCID 68966264, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

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.

Sources & evidence

ORD record
ord-3f88fa8e47e943378c179e83d1f8aa0e
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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