Triphenylphosphine → HCID 57570897, compound

HRID 1695322Notes

Reaction equation

C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.O[CH2:33][CH2:34][CH:35]([CH2:39][CH2:40][OH:41])[CH2:36][CH2:37][OH:38].[C:42]([OH:45])(=[S:44])[CH3:43]>C1COCC1>[C:42]([S:44][CH2:33][CH2:34][CH:35]([CH2:39][CH2:40][OH:41])[CH2:36][CH2:37][OH:38])(=[O:45])[CH3:43]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of triphenylphosphine (1.77 g, 6.8 mmol) in anhydrous THF (15 mL) was added diethyl azodicarboxylate (2.2 M in toluene, 2.4 mL, 5.4 mmol) dropwise at 0° C. After stirred at 0° C. for 55 minutes, a solution of 3-(2-hydroxyethyl)pentane-1,5-diol (740 mg, 5 mmol) and thioacetic acid (335 μL, 4.5 mmol) in dry THF (7 mL) was added dropwise. After 1 hour the ice/water bath was removed and the reaction was stirred at room temperature for 16 hours. The solvents were removed by rotary evaporation in vacuo. The residue was purified by flash chromatography (CHCl3/MeOH, 20:1, 15:1, 10:1, 4:1) to give 3-(2-acetylthioethyl)pentane-1,5-diol as white solid (350 mg) and recovered starting material triol (406 mg). 1H NMR (400 Hz, CDCl3): δ 3.65-3.63 (m, 4H), 3.45 (bs, 2H), 2.84-2.80 (m, 2H), 2.28 (s, 3H), 1.73-1.67 (m, 1H), 1.55-1.49 (m, 6H). MS (ESI): m/z 229.0 (M+Na)+.

Workup

customAfter 1 hour the ice/water bath was removed
stirringthe reaction was stirred at room temperature for 16 hours
customThe solvents were removed by rotary evaporation in vacuo
customThe residue was purified by flash chromatography (CHCl3/MeOH, 20:1, 15:1, 10:1, 4:1)

Sources & evidence

ORD record: ord-44f1b7c4eaf04bc19a73864ba7009ec9
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163736B2

Reaction notes

Loading…