Dichloromethane → HCID 24766581, compound

HRID 552882Notes

Reaction equation

HRID 552882 reaction equation
[CH3:1][O:2][C:3]1[CH:31]=[CH:30][C:6]([C:7]([O:22][CH2:23][C:24]([CH2:28][OH:29])([CH3:27])[CH2:25][OH:26])([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.[H-].[Na+].[CH2:34](Br)[C:35]#[CH:36].C(Cl)Cl>C1COCC1.O>[CH3:15][O:14][C:11]1[CH:12]=[CH:13][C:8]([C:7]([O:22][CH2:23][C:24]([CH2:28][O:29][CH2:36][C:35]#[CH:34])([CH3:27])[CH2:25][OH:26])([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:31][CH:30]=2)=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 24766692HCID 24766692, compound

Product 1

HCID 24766581HCID 24766581, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-O-(4,4′-dimethoxytrityl)-2-hydroxymethyl-2-methyl-1,3-propanediol 16 (620 mg, 1.47 mmol) was dissolved in anhydrous THF (6 mL) and sodium hydride (60% in oil, 590 mg, 14.7 mmol) was added. After 10 min stirring, propargyl bromide (80% in toluene, 650 mL, 5.9 mmol) was added and the mixture was stirred at RT for 1 h. Then CH2Cl2 was added (100 mL) and 2 mL of water. Organic layer was washed with water (2×100 mL) and dried over Na2SO4. After evaporation the residue was purified by flash chromatography using an increasing amount of ethyl acetate (10% to 50%) in cyclohexane containing 1% of triethylamine.

Workup

  1. stirringthe mixture was stirred at RT for 1 h
  2. washOrganic layer was washed with water (2×100 mL)
  3. dry with materialdried over Na2SO4
  4. customAfter evaporation the residue
  5. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-05479efc51e84ea89c3b6f719f19469b
Source dataset
uspto-grants-2011_05
Patent number
US07951926B2

Reaction notes

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