1-Propanol → HCID 21678418, compound

HRID 2293617Notes

Reaction equation

HRID 2293617 reaction equation
[Si:1]([O:8][CH2:9][CH:10]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH:11]=[O:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(Cl)(=O)C(Cl)=O.C(O)CC.C(N(CC)CC)C>C(Cl)Cl.CS(C)=O.O>[Si:1]([O:8][CH2:9][CH:10]([CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH2:11][OH:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 10311-PropanolHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 10850249HCID 10850249, compound

Product 1

HCID 21678418HCID 21678418, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

preparation of 3-(tert-Butyldimethylsilyloxy)-2-benzylpropanal (4). Dimethylsulfoxide (3 ml) was added dropwise to a solution of 1.10 g (8.67 mmol) of oxalyl chloride in 30 ml of methylene chloride at -78° C. This solution was stirred and a solution of 2.08 g (7.42 mmol) of the propanol it in 10 ml of dimethylsulfoxide was added. The resulting mixture was stirred for 20 minutes and then 7.6 ml (54.4 mmol) of triethylamine was added. After being stirred for an additional 20 minutes, the mixture was poured into 100 ml of water. The layers were separated. The aqueous phase was extracted with methylene chloride. The combined organic phases were dried and concentrated. The residue was purified on a silica gel column with 3:2 ether/hexane to give 1.84 g (90%) of 3 as a colorless liquid; 1H NMR (CDCl3) δ0.12 (s, 6H), 0.91 (s, 9H), 2.60 (m, 1H), 2.71 (m, 1H), 2.98 (m, 2H), 3.63 (m, 1H), 3.81 (m, 1H), 7.09 (m, 5H); IR (neat); 2931, 2860, 1730, 1471, 1255, 1100, 846 cm-1.

Workup

  1. stirringThe resulting mixture was stirred for 20 minutes
  2. stirringAfter being stirred for an additional 20 minutes
  3. customThe layers were separated
  4. extractionThe aqueous phase was extracted with methylene chloride
  5. customThe combined organic phases were dried
  6. concentrationconcentrated
  7. customThe residue was purified on a silica gel column with 3:2 ether/hexane

Sources & evidence

ORD record
ord-5c6d65b1aa3a46e0a1e0c5aac013ae55
Source dataset
uspto-grants-1997_11
Patent number
US05686565

Reaction notes

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