Toluene → methyl (S)-8-(benzyloxy)-4-(formylmethyl)octanoate

HRID 465624Notes

Reaction equation

HRID 465624 reaction equation
[CH2:1]([C@@H:4]([CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:5][CH2:6][C:7]([O:9][CH3:10])=[O:8])[CH:2]=C.C1(C)C=CC=CC=1.I([O-])(=O)(=O)=[O:31].[Na+]>O1CCCC1.O.[Os](=O)(=O)(=O)=O>[CH2:16]([O:15][CH2:14][CH2:13][CH2:12][CH2:11][C@H:4]([CH2:1][CH:2]=[O:31])[CH2:5][CH2:6][C:7]([O:9][CH3:10])=[O:8])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 3

HCID 1140TolueneHCID 10402792methyl 4(S)-allyl-8-(benzyloxy)octanoateHCID 23667635Sodium periodate

Product 1

HCID 10357812methyl (S)-8-(benzyloxy)-4-(formylmethyl)octanoate

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl (S)-4-allyl-8-(benzyloxy)-octanoate (2.37 g, 7.8 mmol) in tetrahydrofuran (70 ml) and water (24 ml) is added a solution of 10 mg/ml of osmium tetroxide in toluene (9.4 ml, 0.37 mmol). Sodium periodate (3.57 g, 16.7 mmol) is added in small portions over a period of 0.5 hour. The mixture is allowed to stir for 1 hour and then poured on water and extracted with ether (3×30 ml). The combined organic extracts are dried, filtered and evaporated to give crude methyl (S)-8-(benzyloxy)-4-(formylmethyl)octanoate; IR (CH2Cl2): 2727, 1724, 1202, 1100 cm-1.

Workup

  1. additionpoured on water
  2. extractionextracted with ether (3×30 ml)
  3. customThe combined organic extracts are dried
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-59d9f02775ed44988e4526256163f4de
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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