Lithium Hydroxide → HCID 67351277, compound

HRID 1676134Notes

Reaction equation

HRID 1676134 reaction equation
C([O:3][C:4]([C:6]1[S:7][C:8]([CH3:16])=[C:9]([CH2:12][C:13]([CH3:15])=[CH2:14])[C:10]=1[CH3:11])=[O:5])C.[Li+].[OH-]>C(O)C>[CH3:11][C:10]1[C:9]([CH2:12][C:13]([CH3:15])=[CH2:14])=[C:8]([CH3:16])[S:7][C:6]=1[C:4]([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67352988HCID 67352988, compound

Product 1

HCID 67351277HCID 67351277, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3,5-dimethyl-4-(2-methyl-allyl)-thiophene-2-carboxylic acid ethyl ester (978 mg, 4.1 mmol) in ethanol (20 mL) is added 3M aq. LiOH (10 mL) and the mixture is stirred at 60° C. for 1 h. The mixture is partitioned between DCM (100 mL) and 1M aq. HCl (75 mL). The aq. phase is re-extracted with DCM (2×50 mL). The combined organic extracts are dried (MgSO4), filtered and evaporated to give 653 mg of 3,5-dimethyl-4-(2-methyl-allyl)-thiophene-2-carboxylic acid as a light yellow powder; LC-MS: tR=0.94 min, [M+1+CH3CN]+=252.04; 1H NMR (CDCl3): δ 11.50 (br. s, 1H), 4.75 (s, 1H), 4.39 (s, 1H), 3.17 (s, 2H), 2.42 (s, 3H), 2.37 (s, 3H), 1.75 (s, 3H).

Workup

  1. customThe mixture is partitioned between DCM (100 mL) and 1M aq. HCl (75 mL)
  2. extractionThe aq. phase is re-extracted with DCM (2×50 mL)
  3. dry with materialThe combined organic extracts are dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-0ea4bed750a247bd8e585ccd4ecc6606
Source dataset
uspto-grants-2011_08
Patent number
US08003800B2

Reaction notes

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