Boron trifluoride etherate → HCID 10685967, compound

HRID 1600841Notes

Reaction equation

C([Li])CCC.[CH2:6]([Si:8]([C:13]#[CH:14])([CH2:11][CH3:12])[CH2:9][CH3:10])[CH3:7].B(F)(F)F.CCOCC.[CH2:24]([O:31][CH2:32][C@@H:33]1[O:35][CH2:34]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[NH4+].[Cl-]>C1COCC1>[CH2:24]([O:31][CH2:32][C@H:33]([OH:35])[CH2:34][C:14]#[C:13][Si:8]([CH2:11][CH3:12])([CH2:9][CH3:10])[CH2:6][CH3:7])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

Conditions

Temperature: -78 °C

Procedure

Butyllithium (48 ml, 1.6 M) was added to triethylsilylacetylene (10.7 g, 76.4 mmol) in THF (90 ml) at -78° C. over 20 min. After 10 min BF3.OEt2 (10 ml, 82 mmol) was added, then after another 10 min (-)-benzyl-(R)-glycidyl ether (8.4 g, 51 mmol) in THF (20 ml) was added over 10 min. The mixture was stirred at -78° C. for 1 h then at 0° C. for 20 min. Saturated NH4Cl was added and the mixture extracted with EtOAc (×3). The combined organic layers were washed with H2O and brine, dried, evaporated, and purified by chromatography to give (R)-5-benzyloxy-4-hydroxy-1-triethylsilyl-1-pentyne (9.4 g, 61%).

Workup

waitat 0° C. for 20 min
extractionthe mixture extracted with EtOAc (×3)
washThe combined organic layers were washed with H2O and brine
customdried
customevaporated
custompurified by chromatography

Sources & evidence

ORD record: ord-8ab5b99a7d5942629a7795854c4dd516
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05977116

Reaction notes

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