Hydrochloric Acid → HCID 22121593, compound

HRID 1858876Notes

Reaction equation

HRID 1858876 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([C:10]1[CH:15]=[C:14]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:13]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:12][C:11]=1[C:26](=[S:28])C)(=[S:9])C.Cl.O>C1COCC1>[SH:9][CH2:7][C:10]1[CH:15]=[C:14]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:13]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:12][C:11]=1[CH2:26][SH:28]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 21226445Aluminium lithium hydride2×HCID 22121613HCID 22121613, compound

Product 1

HCID 22121593HCID 22121593, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 250 mL two necked round bottom flask equipped with a magnetic stir bar and a reflux condenser was charged with 0.28 g (7.5 mmol) of lithium aluminum hydride (LAH) and 10 mL of dry THF. The apparatus was purged with argon and a solution of 5e (0.98 g; 2.5 mmol) in dry THF was transferred via cannula to the LAH suspension under argon. The mixture was refluxed under argon for 2 h. After cooling the flask to rt, ice cold water was added dropwise carefully. Upon observation of a white precipitate, conc. HCl was rapidly added, followed by more cold water. The aqueous layer was extracted with a mixture of hexanes/Et2 0 (3×50 mL). The organic extracts were combined together, washed with saturated NaHCO3 (2×50 mL), brine (1×50 mL), dried over MgSO4 and concentrated by rotary evaporation. The residual oil was chromatographed on silica gel using a mixture of hexanes/Et2O (60/1) and gave 0.61 g (2.0 mmol, 80% yield) of 5f as a colorless liquid. 1H NMR (300 MHz, CDCl3): δ 0.91 (6H, t, J=7 Hz, CH3), 1.36-1.57 (12H, m), 1.85 (1H, t, SH), 2.53 (4H, t, J=8 Hz, CH2Ar), 3.79 (4H, d, SCH2), 7.04 (2H, s, Ar--H). 13C NMR (75 MHz, CDCl3): δ 14.0, 22.5, 25.8, 30.9, 31.9, 32.2, 130.32, 130.38, 135.7 and 140.3.

Workup

  1. customThe apparatus was purged with argon
  2. temperatureThe mixture was refluxed under argon for 2 h
  3. additionice cold water was added dropwise carefully
  4. extractionThe aqueous layer was extracted with a mixture of hexanes/Et2 0 (3×50 mL)
  5. washwashed with saturated NaHCO3 (2×50 mL), brine (1×50 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated by rotary evaporation
  8. customThe residual oil was chromatographed on silica gel using
  9. additiona mixture of hexanes/Et2O (60/1)

Sources & evidence

ORD record
ord-1b195395d4b6429ca2835462290835b3
Source dataset
uspto-grants-2000_11
Patent number
US06153322

Reaction notes

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