Tetrahydrofuran → HCID 178467440, compound

HRID 928127Notes

Reaction equation

HRID 928127 reaction equation
[OH:1][C:2]([C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15](OCCCC)=[O:16])[CH2:11][CH2:10]1)([C:4]1[S:5][CH:6]=[CH:7][N:8]=1)[CH3:3].C1COCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CO>[OH:16][CH2:15][C@H:12]1[CH2:13][CH2:14][C@H:9]([C:2]([C:4]2[S:5][CH:6]=[CH:7][N:8]=2)([OH:1])[CH3:3])[CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydrideHCID 178451153HCID 178451153, compound

Product 1

HCID 178467440HCID 178467440, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
23 °C

Procedure

Butyl trans-4-[1-hydroxy-1-(1,3-thiazol-2-yl)ethyl]cyclohexanecarboxylate (150 mg, 0.482 mmol) was placed in a vial under an atmosphere of nitrogen and THF (2 mL) was added. Lithium aluminum hydride (3.5 M in THF, 0.270 mL, 0.945 mmol) was added. After 20 min of stirring at 23° C. the reaction was diluted carefully with methanol (5 mL) via dropwise addition. The resulting white suspension was filtered through CELITE, and the filtrate was concentrated to afford 1-[trans-4-(hydroxymethyl)cyclohexyl]-1-(1,3-thiazol-2-yl)ethanol, which was used in subsequent synthetic transformations without purification. MS ESI calc'd. for C12H19NO2S [M+H]+ 242. found 242.

Workup

  1. additionwas added
  2. filtrationThe resulting white suspension was filtered through CELITE
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-b364bfbe297045629c3e357e4f18884e
Source dataset
uspto-grants-2016_03
Patent number
US09290490B2

Reaction notes

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