Water → (4-(Thiophen-3-yl)phenyl)methanol

HRID 530538Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].[S:7]1[CH:11]=[CH:10][C:9]([C:12]2[CH:20]=[CH:19][C:15]([C:16](O)=[O:17])=[CH:14][CH:13]=2)=[CH:8]1.O.[OH-].[K+]>C1COCC1>[S:7]1[CH:11]=[CH:10][C:9]([C:12]2[CH:20]=[CH:19][C:15]([CH2:16][OH:17])=[CH:14][CH:13]=2)=[CH:8]1

Participants

Conditions

Temperature: 0 °C

Procedure

Under nitrogen atmosphere, at 0° C., to a stirring mixture of LiAlH4 (2.0 M THF solution, 3.92 mL, 7.84 mmol) in dry THF (6.0 mL), commercially available 4-(3-thienyl)-benzoic acid (0.4 g, 1.96 mmol) in dry THF (30 mL) was added dropwise. The mixture was left to react at rt for 4 h, then at 0° C. H2O (0.30 mL), 3.0 M KOH solution (0.30 mL) and H2O (1.0 mL) were very slowly added. The mixture was stirred for 1 h at 0° C., filtered to remove the solid residue, and the organic phase dried over Na2SO4. The organic solution was again filtered and concentrated to dryness, affording the title compound (0.222 g, 65%), which was used in the next step without any further purification. 1H NMR (DMSO-d6): δ 4.51 (d, J=5.75 Hz, 2H), 5.17 (t, J=5.75 Hz, 1H), 7.35 (d, J=8.1 Hz, 2H), 7.52-7.57 (m, 1H), 7.63 (dd, J=2.9, 5.0 Hz, 1H), 7.67 (d, J=8.1 Hz, 2H), 7.81-7.86 (m, 1H).

Workup

additionwas added dropwise
waitThe mixture was left
customto react at rt for 4 h
customat 0° C
filtrationfiltered
customto remove the solid residue
dry with materialthe organic phase dried over Na2SO4
filtrationThe organic solution was again filtered
concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-2a0ed80c959241d787782187f05828be
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09353075B2

Reaction notes

Loading…