Sodium Hydroxide → (6-Methoxy-2,3-dihydro-1-benzofuran-2-yl)methanol

HRID 278449Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]2[CH2:7][CH:8]([C:10](O)=[O:11])[O:9][C:5]=2[CH:4]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1.CCOC(C)=O.O>[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]2[CH2:7][CH:8]([CH2:10][OH:11])[O:9][C:5]=2[CH:4]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of (RS)-6-methoxy-2,3-dihydro-benzofuran-2-carboxylic acid (158 mg, 0.813 mmol) in THF (2 ml) was added dropwise in a 0° C. suspension of LiAlH4 (31 mg, 0.813 mmol) in THF (2 ml). After 30 min stirring at 0° C., the reaction mixture was allowed to reflux for 30 minutes. The reaction mixture was then cooled to 0° C. and treated successively with H2O (0.05 ml), 5N NaOH (0.05 ml), H2O (0.15 ml). After 20 minutes stirring at room temperature, EtOAc was added followed by Na2SO4. The so obtained solid was filtered and the filtrate was evaporated. The residue was chromatographed over SiO2 (Merck 230-400 mesh) eluting with nHexane-EtOAc (4:1) to provide (RS)-(6-methoxy-2,3-dihydro-benzofuran-2-yl)-methanol (102 mg, 70%) as a colorless oil, MS:m/e=180 (M+).

Workup

temperatureto reflux for 30 minutes
temperatureThe reaction mixture was then cooled to 0° C.
stirringAfter 20 minutes stirring at room temperature
customThe so obtained solid
filtrationwas filtered
customthe filtrate was evaporated
customThe residue was chromatographed over SiO2 (Merck 230-400 mesh)
washeluting with nHexane-EtOAc (4:1)

Sources & evidence

ORD record: ord-cbcb01bf856d47a7917da13fea8e44e8
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06359138B1

Reaction notes

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