Phosphorus oxychloride → HCID 86753269, compound

HRID 400221Notes

Reaction equation

[C:1]([Si:5]([CH3:21])([CH3:20])[O:6][C@H:7]1[CH2:15][CH2:14][CH2:13][C@@:12]2([CH3:16])[C@H:8]1[CH2:9][CH2:10][C@@H:11]2[C@@H:17](O)[CH3:18])([CH3:4])([CH3:3])[CH3:2].O=P(Cl)(Cl)Cl>N1C=CC=CC=1>[C:1]([Si:5]([CH3:21])([CH3:20])[O:6][C@H:7]1[CH2:15][CH2:14][CH2:13][C@@:12]2([CH3:16])[C@H:8]1[CH2:9][CH2:10]/[C:11]/2=[CH:17]\[CH3:18])([CH3:3])([CH3:4])[CH3:2].[C:1]([Si:5]([CH3:21])([CH3:20])[O:6][C@H:7]1[CH2:15][CH2:14][CH2:13][C@@:12]2([CH3:16])[C@H:8]1[CH2:9][CH2:10]/[C:11]/2=[CH:17]\[CH3:18])([CH3:3])([CH3:4])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

1.43 g (4.58 mmol) of (S)-1-[(1S,3aR,4S,7aR)-4-(tert-Butyldimethyl-silanyloxy)7a-methyl-octahydro-inden-1-yl]ethanol was dissolved in 15 ml pyridine and cooled to 0° C. 420 μl of POCl3 were added slowly. The reaction mixture was stirred at room temperature overnight then poured into a buffer at pH 4, extracted with n-hexane. The organic solution was washed with brine, dried over sodium sulfate and evaporated to dryness. The residue was purified by column chromatography (eluent: n-hexane) to yield 516 mg (39%) of (E)-(3aR,4S,7aS)-4-(tert-Butyl-dimethyl-silanyloxy)-1-ethylidene-7a-methyl-octahydro-indene (E)-(3aR,4S,7aS)-4-(tert-Butyldimethyl-silanyloxy)-1-ethylidene-7a-methyl-octahydro-indene as a colourless oil.

Workup

additionthen poured into a buffer at pH 4
extractionextracted with n-hexane
washThe organic solution was washed with brine
dry with materialdried over sodium sulfate
customevaporated to dryness
customThe residue was purified by column chromatography (eluent: n-hexane)

Sources & evidence

ORD record: ord-019869e5762941008629b6faa1717d85
Source dataset: uspto-grants-1998_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05827883

Reaction notes

Loading…