Tributylstannane → 1-Tri-n-butylstannyl-4-p-fluorophenoxy-3-trimethylsilyloxy-trans-1-butene

HRID 2083522Notes

Reaction equation

[F:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][CH2:7][CH:8]([O:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[C:9]#[CH:10])=[CH:4][CH:3]=1.[CH2:18]([SnH:22]([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:23][CH2:24][CH2:25][CH3:26])[CH2:19][CH2:20][CH3:21]>N(C(C)(C)C#N)=NC(C)(C)C#N>[CH2:27]([Sn:22]([CH2:18][CH2:19][CH2:20][CH3:21])([CH2:23][CH2:24][CH2:25][CH3:26])/[CH:10]=[CH:9]/[CH:8]([O:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[CH2:7][O:6][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:17][CH:16]=1)[CH2:28][CH2:29][CH3:30]

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 2.52 g (10 mmoles) of 3-trimethylsilyloxy-4-p-fluorophenoxy-1-butyne (Example 158), 2.91 g (10 mmoles) of tri-n-butyl-tin hydride, and 10 mg of azobisisobutyronitrile is heated, under an argon atmosphere, with stirring, for 2 hours at 140° C. After cooling to room temperature, the crude reaction mixture is fractionally distilled at 180°-185° C (0.05 mm), to give 4.6 g (85%) of the subject product as a colorless liquid.

Workup

temperatureis heated, under an argon atmosphere
temperatureAfter cooling to room temperature
customthe crude reaction mixture
distillationis fractionally distilled at 180°-185° C (0.05 mm)

Sources & evidence

ORD record: ord-170be3099042469cb43af04ef3b69527
Source dataset: uspto-grants-1978_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04085272

Reaction notes

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