Diethyl Ether → 4-(2-Butyl-benzofuran-3-ylmethyl)-phenol

HRID 1871350Notes

Reaction equation

HRID 1871350 reaction equation
[CH2:1]([C:5]1[O:6][C:7]2[CH:22]=[CH:21][CH:20]=[CH:19][C:8]=2[C:9]=1[CH:10](O)[C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)[CH2:2][CH2:3][CH3:4].C([SiH](CC)CC)C.B(F)(F)F.CCOCC>CC#N>[CH2:1]([C:5]1[O:6][C:7]2[CH:22]=[CH:21][CH:20]=[CH:19][C:8]=2[C:9]=1[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6356Boron trifluorideHCID 12052TriethylsilaneHCID 234456214-[(2-Butyl-benzofuran-3-yl)-hydroxy-methyl]-phenol

Product 1

HCID 234456454-(2-Butyl-benzofuran-3-ylmethyl)-phenolYield 89.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

At -10° C., to a stirred solution of 4-[(2-butyl-benzofuran-3-yl)-hydroxy-methyl]-phenol (2.78 g, 9.39 mmol) in CH3CN was added portionwise triethylsilane (two×1.50 mL, 18.78 mmol total, @ 0.5 h interval). To the reaction was added BF3. Et2O (1.19 mL, 9.39 mmol) and the reaction was stirred for 10 min. The reaction was quenched with sat. aq. K2CO3 and extracted with CH2Cl2. The organic extracts were washed with brine (3×), dried (MgSO4) and concentrated. Purification on silica gel gave 2.35 g (89%) the title compound as a white solid, mp 67-70° C. (DMSO-d6) δ 0.87 (t, 3 H), 1.31 (sextet, 2 H), 1.62 (quintet, 2 H), 2.78 (t, 2 H), 3.84 (s, 2 H), 6.64 (d, 2 H), 7.02 (d, 2 H), 7.09 (dt, 1 H), 7.16 (dt, 1 H), 7.31 (d, 1 H), 7.42 (d, 1 H), 9.16 (s, 1 H). IR (KBr) 3300, 2950, 1610, 1510 and 1450 cm-1. mass spectrum (EI) m/z 280 (M+).

Workup

  1. customThe reaction was quenched with sat. aq. K2CO3
  2. extractionextracted with CH2Cl2
  3. washThe organic extracts were washed with brine (3×)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customPurification on silica gel

Sources & evidence

ORD record
ord-7a42c9bb1ded4c3383b72b4ab8525ca6
Source dataset
uspto-grants-2000_08
Patent number
US06103708

Reaction notes

Loading…