Sodium hydride → HCID 10562118, compound

HRID 863766Notes

Reaction equation

HRID 863766 reaction equation
[H-].[Na+].C[C:4]1([CH3:11])[O:8][C@H:7]([CH2:9][OH:10])[CH2:6][O:5]1.[H][H].[CH3:14][O:15][C:16]1[CH:17]=C([CH:21]=[CH:22][C:23]=1[O:24][CH3:25])CCl>CS(C)=O.O1CCCC1.C(OCC)C>[CH3:14][O:15][C:16]1[CH:17]=[C:11]([CH:21]=[CH:22][C:23]=1[O:24][CH3:25])[CH2:4][O:5][CH2:6][C@H:7]([OH:8])[CH2:9][OH:10]

Participants

8

Reactant 4

HCID 24758Sodium hydrideHCID 81740Veratryl chlorideHCID 736056(R)-SolketalHCID 178418361HCID 178418361, compound

Product 1

HCID 10562118HCID 10562118, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolvent2×HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To the suspension of Sodium hydride (60% oil dispersion, 4.85 g) in dry Dimethyl sulfoxide (100 ml), solution of (R)-(-)-2,2-Dimethyl-1,3-dioxolane-4-methanol (10.68 g) in dry Tetrahydrofuran (30 ml) was added dropwise under Nitrogen atmosphere at room temperature. After evolution of Hydrogen stopped, solution of 3.4-Dimethoxybenzyl chloride (16.42 g) in dry Dimethyl sulfoxide (30 ml) was added dropwise under the same condition. After 10 hrs of stirring, the reaction mixture was diluted with Diethyl ether, washed with water, followed by brine and then dried over Magnesium sulfate, then 1N-Hydrochloric acid (50 ml) and Tetrahydrofuran (100 ml) was added to the residue and stirred for 6 hrs. The reaction mixture was neutralized with Sodium hydrogen carbonate, extracted with Chloroform and dried over Magnesium sulfate. The title compound was obtained after column purification (Hexane+Ethyl acetate 1:2~Ethyl acetate+Acetone (10:1) as oil. Yield: 18.31 g (94%). NMR (CDCl3): 2.16 (1H, br, s), 3.55 (2H, m), 3.67 (2H, m), 3.88 (3H, s), 3.89 (3H, s), 3.92 (1H, m), 4.49 (2H, s). IR (Neat), cm-1 : 3385, 2910, 1505. [α]25D =+1.0° (C=2.0, Chloroform).

Workup

  1. additionwas added dropwise under Nitrogen atmosphere at room temperature
  2. washwashed with water
  3. dry with materialdried over Magnesium sulfate
  4. addition1N-Hydrochloric acid (50 ml) and Tetrahydrofuran (100 ml) was added to the residue
  5. stirringstirred for 6 hrs
  6. extractionextracted with Chloroform
  7. dry with materialdried over Magnesium sulfate

Sources & evidence

ORD record
ord-ceac78787f044525a30cd7915e58aca3
Source dataset
uspto-grants-1996_10
Patent number
US05561126

Reaction notes

Loading…