2,3-dihydro-1H-indene-5-carboxylic acid → (2,3-dihydro-1H-inden-5-yl)methanol

HRID 1847571Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of LAH (72.8 g, 1.92 mol) in THF (2.5 L) at 0° C. was slowly added 2,3-dihydro-1H-indene-5-carboxylic acid (100.0 g, 0.62 mol). The reaction mixture was stirred at 0° C. for 1 h. Then the reaction was quenched with H2O (72 ml) and NaOH (68 ml, 20%). The mixture was filtered and the organic layer was dried over Na2SO4, evaporated in vacuo and the residue was purified by column chromatography (petroleum ether:ethyl acetate=10:1) to give the desired product (82.0 g, 90%). 1H NMR (CDCl3, 300 MHz); δ 2.03-2.13 (m, 2H), 2.91 (t, J=7.5 Hz, 4H), 4.64 (s, 2H), 7.13 (d, J=7.5, 1H), 7.18-7.24 (m, 2H).

Workup

customat 0° C.
customThen the reaction was quenched with H2O (72 ml) and NaOH (68 ml, 20%)
filtrationThe mixture was filtered
dry with materialthe organic layer was dried over Na2SO4
customevaporated in vacuo
customthe residue was purified by column chromatography (petroleum ether:ethyl acetate=10:1)

Sources & evidence

ORD record: ord-a350abf5f05846c1ae800e25d288aaf0
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952050B2

Reaction notes

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