1,3-Thiazole-2-carbaldehyde → HCID 59774862, compound

HRID 2422511Notes

Reaction equation

[Li]C(C)(C)C.[CH3:6][O:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[CH:11]=1.[S:17]1[CH:21]=[CH:20][N:19]=[C:18]1[CH:22]=[O:23]>C1COCC1>[CH3:6][O:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]([CH3:16])[CH:13]=[CH:14][C:15]=1[CH:22]([C:18]1[S:17][CH:21]=[CH:20][N:19]=1)[OH:23]

Participants

Conditions

Temperature: 0 °C

Procedure

To a cooled (0° C.) solution of t-BuLi (1.7 M in pentane, 5.0 mL, 8.5 mmol), 1-(methoxymethoxy)-3-methylbenzene (see example 33, step 1) was added dropwise (1.18 g, 7.73 mmol), maintaining the internal temperature below 16° C. The suspension was stirred at 0° C. for 1 h, cooled to −78° C., and THF (15 mL) was added. A solution of 1,3-thiazole-2-carboxaldehyde (0.962 g, 8.5 mmol) was added and the cooling bath was removed. The reaction mixture was allowed to warm to 0° C., extracted twice with EtOAc from NH4Cl, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (30-50% EtOAc in hexanes) to afford the title compound. 1H NMR (400 MHz, acetone-d6): 7.77 (d, 1H), 7.48 (s, 1H), 7.33 (d, 1H), 6.95 (s, 1H), 6.83 (d, 1H), 6.36 (d, 1H), 5.32 (d, 1H), 5.21 (s, 2H), 3.38 (s, 3H), 2.32 (s, 3H).

Workup

additionwas added dropwise (1.18 g, 7.73 mmol)
temperaturemaintaining the internal temperature below 16° C
temperaturecooled to −78° C.
customthe cooling bath was removed
temperatureto warm to 0° C.
extractionextracted twice with EtOAc from NH4Cl
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by flash chromatography (30-50% EtOAc in hexanes)

Sources & evidence

ORD record: ord-3c8412b9ceec40f3bc372a029dc07bee
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960409B2

Reaction notes

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