Benzyl Alcohol → HCID 59336573, compound

HRID 12011Notes

Reaction equation

HRID 12011 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N([CH:15]([CH3:17])[CH3:16])CC)(C)C.Cl[Si:19](Cl)([CH:23]([CH3:25])[CH3:24])[CH:20](C)[CH3:21].[C-]#[C-].[Li+].[Li+].C(N)CN>C1COCC1.O>[CH2:1]([O:8][Si:19]([C:20]#[CH:21])([CH:15]([CH3:16])[CH3:17])[CH:23]([CH3:25])[CH3:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 81531DiisopropylethylamineHCID 2758384DiisopropyldichlorosilaneHCID 178511344HCID 178511344, compound

Product 1

HCID 59336573HCID 59336573, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

A solution of benzyl alcohol (0.1 mL, 1.0 mmol) in THF (0.5 mL) was added dropwise to a cooled (−78° C.) solution of diisopropylethylamine (1 mL), dichlorodiisopropylsilane (0.3 mL, 1.62 mmol) in THF (4 mL). The solution was stirred for 3 h (−78→−20° C.). The mixture was cooled down to −78° C. and lithiumacetylid-ethylendiamin-complex (250 mg, 2.71 mmol) was added. The reaction mixture was stirred for 5 h (−78→20° C.). Water (4 mL) was added. The mixture was extracted with dichloromethane (20 mL). The organic phase was dried (Na2SO4) and concentrated. Compound 14a (100 mg, 41%) was obtained after flash chromatography. 1H-NMR (CDCl3): δ 7.4 (5H, 5×HC═), 5.0 (2H, CH2), 2.6 (1H, CH), 1.0 (14H, 2×CH, 2×CH3).

Workup

  1. temperatureThe mixture was cooled down to −78° C.
  2. stirringThe reaction mixture was stirred for 5 h (−78→20° C.)
  3. extractionThe mixture was extracted with dichloromethane (20 mL)
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-befd86f60b4344fb96ef09d3a9c92e0e
Source dataset
uspto-grants-2010_06
Patent number
US07727713B2

Reaction notes

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