Tributyltin Chloride → 2-(Diethoxymethyl)-5-(tributylstannyl) thiophene

HRID 1604453

Reaction equation

[CH2:1]([O:3][CH:4]([O:10][CH2:11][CH3:12])[C:5]1[S:6][CH:7]=[CH:8][CH:9]=1)[CH3:2].C([Li])CCC.[CH2:18]([Sn:22](Cl)([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:23][CH2:24][CH2:25][CH3:26])[CH2:19][CH2:20][CH3:21]>O1CCCC1>[CH2:11]([O:10][CH:4]([O:3][CH2:1][CH3:2])[C:5]1[S:6][C:7]([Sn:22]([CH2:23][CH2:24][CH2:25][CH3:26])([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:18][CH2:19][CH2:20][CH3:21])=[CH:8][CH:9]=1)[CH3:12]

Participants

Conditions

Temperature: -78 °C

Procedure

18.6 g (100 mmol) of 2-(diethoxymethyl) thiophene in 100 ml of tetrahydrofuran ("THF") was placed in a 2-neck flask equipped with dropping funnel. The solution was cooled to -78° C. under nitrogen atmosphere and added 62.5 mL of 1.6 M n-butyl lithium (100 mmol) dropwise through dropping funnel in 1 hr. The reaction mixture was stirred at -78° C. for 1 hr and gradually warmed up to room temperature. After stirred for 30 minutes, the mixture was again cooled to -78° C. and added dropwise a THF (50 mL) solution of 32.5 g (100 mmol) of tributyl tin chloride with continual stirring. Gradually warmed up to room temperature, the mixture was stirred for another 10-12 hrs at room temperature and then concentrated. Reduced pressure distillation yielded 36.8 g (80%) of 2-(diethoxymethyl)-5-(tributylstannyl) thiophene (bp 195° C./1 torr).

Workup

customequipped
customin 1 hr
temperaturegradually warmed up to room temperature
stirringAfter stirred for 30 minutes
temperaturethe mixture was again cooled to -78° C.
temperatureGradually warmed up to room temperature
stirringthe mixture was stirred for another 10-12 hrs at room temperature
concentrationconcentrated
distillationReduced pressure distillation

Sources & evidence

ORD record: ord-c01d9dfaaaf344c0bc5c37c21112a344
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05994394

Linked notes

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