Tetrahydrofuran → HCID 66879181, compound
Reaction equation
S1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3][CH2:2]1.C1N=CN(C(N2C=N[CH:19]=[CH:18]2)=O)C=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH3:32][CH2:33][O:34][C:35]([CH3:37])=[O:36].C1C[O:41][CH2:40]C1>>[CH2:33]([O:34][C:35](=[O:36])[CH2:37][C:40]([CH:2]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH2:18][CH3:19])=[O:8])[CH2:3]1)=[O:41])[CH3:32]Participants
Procedure
To a solution of tetrahydro-2H-thiopyran-4-carboxylic acid (2.0 g, 13.7 mmol) in THF (25 mL) was added CDI (2.66 g, 1.20 eq). The mixture was stirred at rt for 1 h. To a solution of LiHMDS (1.0 M in THF, 29 mL) in THF (30 mL) at −78° C. was added EtOAc (2.90 mL) dropwise. The mixture was stirred at −78° C. for 1 h, then the acid/CDI mixture was added through an addition funnel over 30 min at −78° C. The mixture was stirred at −78° C. for 1 h then allowed to warm up to rt over 2 h. The reaction was quenched with saturated NH4Cl and extracted with diethyl ether. The combined organic layers were dried over Na2SO4, filtered and concentrated. The residue was purified by Biotage (CH2Cl2/EtOAc, 100:1 to 10:1) to give the title compound as a clear oil. LC/MS RT=1.73 min (5 min method). Mass calculated for, M+H 217.08, observed 217.08.
Workup
- stirringThe mixture was stirred at −78° C. for 1 h
- stirringThe mixture was stirred at −78° C. for 1 h
- temperatureto warm up to rt over 2 h
- customThe reaction was quenched with saturated NH4Cl
- extractionextracted with diethyl ether
- dry with materialThe combined organic layers were dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by Biotage (CH2Cl2/EtOAc, 100:1 to 10:1)
Sources & evidence
- ORD record
- ord-bf61b1d1cecd4742aae5f6e76ae84033
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08609675B2
Reaction notes
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