Sodium Cyanide → 8-t-Butyl-3-cyano-1-oxaspiro(4,5)decane

HRID 232548Notes

Reaction equation

[C:1]([CH:5]1[CH2:25][CH2:24][C:8]2([O:12][CH2:11][CH:10](OS(C3C=CC(C)=CC=3)(=O)=O)[CH2:9]2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[C-:26]#[N:27].[Na+]>CN(C=O)C>[C:1]([CH:5]1[CH2:6][CH2:7][C:8]2([O:12][CH2:11][CH:10]([C:26]#[N:27])[CH2:9]2)[CH2:24][CH2:25]1)([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 8-t-butyl-3-(p-toluenesulfonyloxy)-1-oxaspiro-(4,5)decane (18.3 g, 50 mmol) and sodium cyanide (4.9 g, 100 mmol) in dry DMF (75 ml) was heated to 100° C. for 6 hours. Light petroleum/ethylacetate 4:1 (50 ml) was added and the mixture was filtrated from insoluble material. The filtrate was then evaporated in vacuo and the resulting residue was taken up in toluene (100 ml). It was washed with water, dried (MgSO4) and evaporated in vacuo to yield a brownish oil (11.0 g) which was Kugelrohr distilled (120°-125° C., 0.015 mbar) to furnish the product as colourless crystals (8.94 g, m.p. 35°-40° C.).

Workup

filtrationthe mixture was filtrated from insoluble material
customThe filtrate was then evaporated in vacuo
washIt was washed with water
dry with materialdried (MgSO4)
customevaporated in vacuo

Sources & evidence

ORD record: ord-3720a0fc21b14aa1a84a3d1dfad4669d
Source dataset: uspto-grants-1997_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05591741

Reaction notes

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