Hydrochloric Acid → 2-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiazol-2-yl)propan-2-ol

HRID 1504796Notes

Reaction equation

[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]([OH:9])([CH3:8])[CH3:7].C([Li])CCC.[CH3:15][C:16]1([CH3:27])[C:20]([CH3:22])([CH3:21])[O:19][B:18](OC(C)C)[O:17]1.Cl>C1COCC1>[CH3:15][C:16]1([CH3:27])[C:20]([CH3:22])([CH3:21])[O:19][B:18]([C:5]2[S:1][C:2]([C:6]([OH:9])([CH3:8])[CH3:7])=[N:3][CH:4]=2)[O:17]1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 2-(1,3-thiazol-2-yl)propan-2-ol (40 g, 0.28 mol) in THF (400 mL) was add n-butyllithium (2.5 M in hexanes, 260 mL, 0.64 mol) dropwise at −78° C. After 30 minutes, 4,4,5,5-tetramethyl-2-(propan-2-yloxy)-1,3,2-dioxaborolane (65 g, 0.35 mol) was added at −78° C. The reaction solution was then stirred at −78° C. After 1 hour, the reaction mixture was quenched with acetic acid, filtered, and concentrated under reduced pressure. The residue was diluted with hydrochloric acid (3.0 M solution in diethyl ether, 110 mL, 0.33 mol) and the mixture was filtered to afford 2-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-thiazol-2-yl]propan-2-ol. MS ESI calc'd. for C12H21BNO3S [M+H]+ 270. found 270. 1H NMR (300 MHz, DMSO-d6): δ 8.01 (s, 1H), 1.49 (s, 6H), 1.28 (s, 12H).

Workup

waitAfter 1 hour
customthe reaction mixture was quenched with acetic acid
filtrationfiltered
concentrationconcentrated under reduced pressure
filtrationthe mixture was filtered

Sources & evidence

ORD record: ord-9ce58a97f9a74a0eb0b110a92bddc7ff
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216173B2

Reaction notes

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