Water → HCID 21880341, compound

HRID 724351Notes

Reaction equation

HRID 724351 reaction equation
[CH3:1][C:2]1[S:6][C:5]2[C:7](=O)[CH:8]([CH:10]([CH3:12])[CH3:11])[CH2:9][C:4]=2[C:3]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O>CCOCC>[CH:10]([C:8]1[CH2:7][C:5]2[S:6][C:2]([CH3:1])=[C:3]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:4]=2[CH:9]=1)([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 21880349HCID 21880349, compound

Product 1

HCID 21880341HCID 21880341, compoundYield 104.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
80 °C

Procedure

A solution of 2-methyl-5-(isopropyl)-3-phenyl-4,5-dihydrocyclopenta[2,1-b]thiophen-6-one (18.5 g, 0.068 mol) in 80 mL of ether was treated with 40 mL of an ether solution of LiAlH4 (1 M, 0.04 mol). After sting for 12 h, water (˜20 mL) was added cautiously and the mixture was filtered through celite. The filter pad was washed with dichloromethane (3×100 mL) and the combined organic fractions were dried (MgSO4). Solvents were evaporated and the residue was dissolved in 150 mL of toluene. p-TSA (1.0 g) was added and the mixture was stirred at 80° C. for 2 h. After cooling, the mixture was washed with a saturated aqueous solution of NaHCO3, brine solution, and dried (MgSO4). Evaporation of solvent gave 18.1 g of product (93% purity by GC/MS). 1H-NMR δ (CD2Cl2): (major isomer) 7.3–7.5 (m, 5H), 6.48 (s, 1H), 3.2 (s, 2H), 2.8 (m, 1H), 2.5 (s, 3H), 1.22 (d, 6H). EIMS: m/z (%) 254 (M+, 55), 239 (100), 224 (25), 211 (5), 191 (5), 178 (9), 165 (7).

Workup

  1. filtrationthe mixture was filtered through celite
  2. washThe filter pad was washed with dichloromethane (3×100 mL)
  3. dry with materialthe combined organic fractions were dried (MgSO4)
  4. customSolvents were evaporated
  5. dissolutionthe residue was dissolved in 150 mL of toluene
  6. additionp-TSA (1.0 g) was added
  7. temperatureAfter cooling
  8. washthe mixture was washed with a saturated aqueous solution of NaHCO3, brine solution
  9. dry with materialdried (MgSO4)
  10. customEvaporation of solvent

Sources & evidence

ORD record
ord-2f85fe487eb94d629585d1dcecd73475
Source dataset
uspto-grants-2006_11
Patent number
US07141637B2

Reaction notes

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