Triisopropyl phosphite → HCID 22969121, compound

HRID 1278849Notes

Reaction equation

HRID 1278849 reaction equation
C(O[CH:5]1[CH:9]2[O:10][C:11]([CH3:14])([CH3:13])[O:12][CH:8]2[CH:7]([CH2:15][O:16][C:17](=[O:19])[CH3:18])[O:6]1)(=O)C.I[Si](C)(C)C.[CH:25]([O:28][P:29]([O:34]C(C)C)[O:30][CH:31]([CH3:33])[CH3:32])([CH3:27])[CH3:26]>ClCCl>[CH:25]([O:28][P:29]([CH:5]1[CH:9]2[O:10][C:11]([CH3:13])([CH3:14])[O:12][CH:8]2[CH:7]([CH2:15][O:16][C:17](=[O:19])[CH3:18])[O:6]1)([O:30][CH:31]([CH3:33])[CH3:32])=[O:34])([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 8304Triisopropyl phosphiteHCID 85247Trimethylsilyl iodideHCID 3475199HCID 3475199, compound

Product 1

HCID 22969121HCID 22969121, compoundYield 54.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of acetic acid 6-acetoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester (623 mg, 2.27 mmol) in dichloromethane (3 mL) was added iodotrimethylsilane (0.35 mL, 2.49 mmol) at −78° C. and the reaction mixture brought to RT. After confirming the disappearance of starting material by TLC, triisopropylphosphite (1.18 mL, 5.68 mmol) was added at −78° C. The reaction mixture was left to warm to RT and stirred overnight. The reaction was quenched with sodium bicarbonate, extracted with dichoromethane, the organic layers concentrated, dried and chromatographed. Elution with 50% ethylacetate/hexanes gave acetic acid 6-(diisopropoxy-phosphoryl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester as a colorless syrup (467 mg, 54%).

Workup

  1. custombrought to RT
  2. additionwas added at −78° C
  3. waitThe reaction mixture was left
  4. customThe reaction was quenched with sodium bicarbonate
  5. extractionextracted with dichoromethane
  6. concentrationthe organic layers concentrated
  7. customdried
  8. customchromatographed
  9. washElution with 50% ethylacetate/hexanes

Sources & evidence

ORD record
ord-14a0aef8c7b04971b228d8b7cb080670
Source dataset
uspto-grants-2002_09
Patent number
US06444656B1

Reaction notes

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