Triphenylphosphine → 9-Acetylthio-3-(2-(3-furyl)ethyl)-spiro[5.5]undecane

HRID 1757221Notes

Reaction equation

O[CH:2]1[CH2:19][CH2:18][C:5]2([CH2:10][CH2:9][CH:8]([CH2:11][CH2:12][C:13]3[CH:17]=[CH:16][O:15][CH:14]=3)[CH2:7][CH2:6]2)[CH2:4][CH2:3]1.[S:20]1C=CC=C1CC(O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC([O:52][CH:53]([CH3:55])C)=O>O1CCCC1>[C:53]([S:20][CH:2]1[CH2:19][CH2:18][C:5]2([CH2:10][CH2:9][CH:8]([CH2:11][CH2:12][C:13]3[CH:17]=[CH:16][O:15][CH:14]=3)[CH2:7][CH2:6]2)[CH2:4][CH2:3]1)(=[O:52])[CH3:55]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 0.200 g of 9-hydroxy-3-(2-(3-furyl)ethyl)-spiro[5.5]-undecane (I-ap, Ex. 38) and 0.11 ml of thiolacetic acid in 9 ml of anhydrous tetrahydrofuran was added to a solution of 0.40 g of triphenylphosphine and 0.30 ml of diisopropyl azodicarboxylate in 1 ml of anhydrous tetrahydrofuran, and the mixture stirred at 0° C. under argon atmosphere for 2 hrs. Silica gel was then added, the mixture was evaporated to dryness and the residue purified by chromatography (SiO2 ; n-hexane/diethylether 90/10) to give 0.120 g of 9-acetylthio-3-(2(3-furyl)ethyl)-spiro[5.5]undecane as a light oil. TLC: Rf=0.72 (SiO2 plates, n-hexane/diethylether 90/10). 1H-NMR (300 MHz, CDCl3, ppm from TMS): 7.40 (1H, m), 7.21 (1H, m), 6.25 (1H, m), 3.48 (1H, m), 2.48 (2H, t), 2.30 (3H, s), 1.90-0.85 (19H, m).

Workup

additionSilica gel was then added
customthe mixture was evaporated to dryness
customthe residue purified by chromatography (SiO2 ; n-hexane/diethylether 90/10)

Sources & evidence

ORD record: ord-fe2d62aea1cf4a7d8fc906640a03deb8
Source dataset: uspto-grants-1995_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05444082

Reaction notes

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