Sulfamic Acid → 2-(2-phenyltetrahydro-2H-pyran-2-yl)acetic acid

HRID 71264Notes

Reaction equation

HRID 71264 reaction equation
[C:1]1([C:7]2([CH2:13][CH:14]=[O:15])[CH2:12][CH2:11][CH2:10][CH2:9][O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)([OH:18])N.Cl([O-])=O.[Na+]>C1COCC1.O>[C:1]1([C:7]2([CH2:13][C:14]([OH:18])=[O:15])[CH2:12][CH2:11][CH2:10][CH2:9][O:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 5987Sulfamic AcidHCID 23668197Sodium ChloriteHCID 866882052-(2-phenyltetrahydro-2H-pyran-2-yl)acetaldehyde

Product 1

HCID 666857082-(2-phenyltetrahydro-2H-pyran-2-yl)acetic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(2-phenyltetrahydro-2H-pyran-2-yl)acetaldehyde (100 mg, 0.490 mmol) and sulfamic acid (57.0 mg, 0.587 mmol) in THF (1.5 mL) was added a solution of sodium chlorite (53.1 mg, 0.587 mmol) in water (1.5 mL) dropwise, and the mixture was stirred at room temperature for 3 hrs. Then the product was extracted with EtOAc (3×) and the combined extracts were washed with brine, dried over Na2SO4, and evaporated to give 2-(2-phenyltetrahydro-2H-pyran-2-yl)acetic acid as oil. LC/MS: m/e 221.14 (M+H)+.

Workup

  1. extractionThen the product was extracted with EtOAc (3×)
  2. washthe combined extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-65086ca25cd44c60bc1357055a651c4f
Source dataset
uspto-grants-2014_09
Patent number
US08822510B2

Reaction notes

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