Sodium Thiosulfate → 2-(Adamantan-1-yl)acetaldehyde

HRID 915717Notes

Reaction equation

HRID 915717 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1C(O)C)[CH2:8]2.CC1(C)N([O])C(C)(C)CCC1.[C:25](O)(=[O:27])[CH3:26].C(O)(=O)C.IC1C=CC=CC=1.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[C:1]12([CH2:26][CH:25]=[O:27])[CH2:10][CH:5]3[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]3)[CH2:8]1)[CH2:2]2

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 2724126TempoHCID 12217721Iodo benzene diacetateHCID 137791421-(2-Adamantyl)ethanol

Product 1

HCID 50860842-(Adamantan-1-yl)acetaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a flask containing 2-adamantyl-1-ethanol (5 g, 27.7 mmol) in CH2Cl2 (28 mL) was added TEMPO (433 mg, 2.77 mmol) followed by iodobenzene diacetate (9.8 g, 30.5 mmol). The reaction was stirred 1 hour and then diluted with CH2Cl2 (100 mL). Saturated aqueous solution of Na2S2O3 (100 mL) was added and extracted with CH2Cl2 (3×50 mL). The combined organics were washed with saturated aqueous NaHCO3 (150 mL) and brine (150 mL), dried over Na2SO4, and concentrated in vacuo. The resulting residue was purified by silica gel chromatography (5% Et2O/pentanes) to provide the title compound, which was identical to the reported literature compound (see Luly et al. (1987) J. Org. Chem. 52: 1487).

Workup

  1. extractionextracted with CH2Cl2 (3×50 mL)
  2. washThe combined organics were washed with saturated aqueous NaHCO3 (150 mL) and brine (150 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by silica gel chromatography (5% Et2O/pentanes)

Sources & evidence

ORD record
ord-4227be24cf5746e1aa4eda1b4c1a83a8
Source dataset
uspto-grants-2007_09
Patent number
US07265249B2

Reaction notes

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