Ethyl (5-bromothiophen-2-yl)(oxo)acetate → Ethyl 2-(5-bromothiophen-2-yl)-2-hydroxyacetate

HRID 1484964Notes

Reaction equation

[Br:1][C:2]1[S:6][C:5]([C:7](=[O:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:4][CH:3]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1.C(OCC)(=O)C>[Br:1][C:2]1[S:6][C:5]([CH:7]([OH:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of ethyl 2-(5-bromothiophen-2-yl)-2-oxoacetate (2.5 g, 9.5 mmol) in tetrahydrofuran (50 mL) was added sodium triacetoxy borohydride (2.5 g, 11.8 mmol, 1.2 eq). After stirring for 1 hour at 60° C., the reaction mixture was diluted with ethyl acetate, washed (brine), dried (Na2SO4), filtered and concentrated to provide ethyl 2-(5-bromothiophen-2-yl)-2-hydroxyacetate (2.5 g, 99.24%). 1H NMR (400 MHz, DMSO-d6): δ 1.19 (t, J=7.0 Hz, 3H), 4.11-4.16 (m, 2H), 5.34 (d, J=5.6 Hz, 1H), 6.50 (d, J=6.0 Hz, 1H), 6.91 (d, J=4.0 Hz, 1H), 7.09 (d, J=4.0 Hz, 1H).

Workup

washwashed (brine)
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-7b9f00d3cccd4cf08445c0302c96ca4d
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422271B2

Reaction notes

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