2,3-Dihydroxybutanedioic Acid → 2-Ethyl-2-thiophen-2-yl-butan-1-ol

HRID 660974Notes

Reaction equation

HRID 660974 reaction equation
COC(=O)C(C)(C1[S:7]C=CC=1)C.C([Al]C[CH:19]([CH3:21])C)C(C)C.[C:22]1([CH3:28])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[C:29]([OH:38])(=O)C(C(C(O)=O)O)O>C(Cl)Cl>[CH2:19]([C:27]([C:26]1[S:7][CH:23]=[CH:24][CH:25]=1)([CH2:22][CH3:28])[CH2:29][OH:38])[CH3:21]

Participants

6

Reactant 4

HCID 8752,3-Dihydroxybutanedioic AcidHCID 1140TolueneHCID 11423980Methyl 2-Methyl-2-(2-thienyl)propanoateHCID 16682954Dibah2×

Product 1

HCID 674847232-Ethyl-2-thiophen-2-yl-butan-1-olYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-methyl-2-thiophen-2-yl-propionic acid methyl ester (3.66 g, 17.2 mmol) in CH2Cl2 (85 mL) at 0° C. is treated with diisobutylaluminum hydrde (Dibal-H, 1.0 M PhMe, 38.0 mL, 384.0 mmol) and warmed to rt overnight. The reaction mixture is carefully poured into 1N tartaric acid (100 mL) and stirred for 3 d. The layers are separated and the aqueous layer is extracted with CH2Cl2 (100 mL). The combined extracts are dried over MgSO4, filtered, and concentrated. The residue is loaded onto silica gel and eluted with hexanes using a gradient of 0% to 75% EtOAc to give 2-ethyl-2-thiophen-2-yl-butan-1-ol (2.87 g, 90%) as a pink oil.

Workup

  1. customThe layers are separated
  2. extractionthe aqueous layer is extracted with CH2Cl2 (100 mL)
  3. dry with materialThe combined extracts are dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. washeluted with hexanes using a gradient of 0% to 75% EtOAc

Sources & evidence

ORD record
ord-0ca980ce97b9452b90fb5beb795eaab4
Source dataset
uspto-grants-2011_12
Patent number
US08084489B2

Reaction notes

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