Hydrochloric Acid → 2-(2-phenylethyl)-2,3-dihydro-1-benzofuran-5-ol

HRID 1535046Notes

Reaction equation

HRID 1535046 reaction equation
C(S)C.[H-].[Li+].[C:6]1([CH2:12][CH2:13][CH:14]2[CH2:18][C:17]3[CH:19]=[C:20]([O:23]C)[CH:21]=[CH:22][C:16]=3[O:15]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl>CN(C)C=O>[OH:23][C:20]1[CH:21]=[CH:22][C:16]2[O:15][CH:14]([CH2:13][CH2:12][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH2:18][C:17]=2[CH:19]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6343EthanethiolHCID 62714Lithium hydrideHCID 15161037HCID 15161037, compound2×

Product 1

HCID 98812472-(2-phenylethyl)-2,3-dihydro-1-benzofuran-5-olYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Ethanethiol (62 gm; 1 mole) was added dropwise to lithium hydride (8 gm; 1 mole) in dimethylformamide (700 mL) under nitrogen atmosphere. 2-(2-phenylethyl)-5-methoxy-2,3-dihydrobenzofuran, E4, (126 gm; 500 mmoles) in dimethylformamide (200 mL) was then added in one portion and the mixture brought to reflux for 3 hours. The mixture was poured into 1N hydrochloric acid and extracted with diethyl ether. The ether layer was separated and backwashed with water twice, dried over MgSO4, filtered and concentrated in vacuo to obtain 123 gm (98%) of 5-hydroxy-2-(2-phenylethyl)-2,3-dihydrobenzofuran, E5, m.p. 56°-58° C.

Workup

  1. temperatureto reflux for 3 hours
  2. extractionextracted with diethyl ether
  3. customThe ether layer was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6492c233f6624afcb09862aecb3a549a
Source dataset
uspto-grants-1992_02
Patent number
US05091533

Reaction notes

Loading…