Carbon Dioxide → HCID 18324166, compound

HRID 2050988Notes

Reaction equation

[CH3:1][C:2]1([CH3:15])[CH2:11][C:10]([CH3:13])([CH3:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7](Br)[CH:8]=2)[S:3]1.C([Li])(C)(C)C.[C:21](=[O:23])=[O:22].O>CCOCC.CCCCC>[CH3:1][C:2]1([CH3:15])[CH2:11][C:10]([CH3:13])([CH3:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:21]([OH:23])=[O:22])[CH:8]=2)[S:3]1

Participants

Conditions

Temperature: -78 °C

Procedure

To a stirred solution of 240 mg (0.84 minol) of 2,2,4,4-tetramethyl-6-bromothiochroman in 1 ml of dry ether at -78° C. was added, dropwise under nitrogen, 1 ml of 1.7M (1.7 mmol) tert-butyl lithium in pentane. The reaction mixture was stirred at -78° C. for a further 2 h and then treated quickly with an excess of dry ice. The reaction mixture was warmed to room temperature and treated with 1 ml of water and 1 ml of ether. The aqueous layer was separated and the organic layer was extracted with 4×5 ml of water. The aqueous extracts were combined, acidified with HCl to a pH of 2 and then extracted with 2×15 ml of ether. The ether extracts were combined, washed with water and saturated NaCl solution and then dried (MgSO4). The ether solution was filtered and the solvent removed in-vacuo to give the title compound as a white solid. PMR (CDCl3): δ1.42 (6H, s), 1.43 (6H, s), 2.03 (2H, s), 7.50 (1H, d, J~8.4 Hz), 7.81 (1H, dd, J~8.4 Hz, 1.8 Hz), 7.89 (1H, d, J~1.8 Hz).

Workup

temperatureThe reaction mixture was warmed to room temperature
customThe aqueous layer was separated
extractionthe organic layer was extracted with 4×5 ml of water
extractionextracted with 2×15 ml of ether
washwashed with water and saturated NaCl solution
dry with materialdried (MgSO4)
filtrationThe ether solution was filtered
customthe solvent removed in-vacuo

Sources & evidence

ORD record: ord-04316ffcf86a4790996b999371e9918a
Source dataset: uspto-grants-1991_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05015658

Reaction notes

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