Methanol → HCID 67084471, compound

HRID 2103611Notes

Reaction equation

HRID 2103611 reaction equation
CC(C[AlH]CC(C)C)C.C([O:12][C:13](=O)/[C:14](/[C:22]1[S:23][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:25][CH:26]=1)=[CH:15]/[CH2:16][CH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1)C.CO>C1COCC1>[CH:17]1([CH2:16]/[CH:15]=[C:14](\[C:22]2[S:23][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:25][CH:26]=2)/[CH2:13][OH:12])[CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14487Diisobutylaluminum hydrideHCID 67084577HCID 67084577, compound

Product 1

HCID 67084471HCID 67084471, compoundYield 104.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add a solution of DIBAL (5.41 mL, 1.2 M in toluene, 6.48 mmol) dropwise over one h to a solution of (Z)-4-cyclopentyl-2-(5-methanesulfonyl-thiophen-2-yl)-but-2-enoic acid ethyl ester (939 mg, max. 2.59 mmol) in THF (5 mL) at to −78 ° C. Then allow the reaction mixture to warm slowly to r.t., and stir for 18 h. Add methanol (1.5 mL) at −78° C. and allow the reaction mixture to warm to r.t. Partition the residue between ethyl acetate (15 mL) and sodium potassium tartrate (15 mL). Then extract the aqueous layer with ethyl acetate. Combine the organic layers, wash them with saturated aqueous sodium chloride solution, dry over sodium sulfate and remove solvent under vacuum to give 812 mg crude product. MS (m/e): 323.0 (M+Na).

Workup

  1. customat −78° C.
  2. temperatureto warm to r.t
  3. customPartition the residue between ethyl acetate (15 mL) and sodium potassium tartrate (15 mL)
  4. extractionThen extract the aqueous layer with ethyl acetate
  5. washwash them with saturated aqueous sodium chloride solution
  6. dry with materialdry over sodium sulfate
  7. customremove solvent under vacuum

Sources & evidence

ORD record
ord-e04d698e449f47ef8b1f69fa234f8ba2
Source dataset
uspto-grants-2009_08
Patent number
US07576108B2

Reaction notes

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