Tributyltin Chloride → HCID 23290213, compound

HRID 366860Notes

Reaction equation

C([Li])CCC.[CH2:6]([O:16][C:17]1[C:21]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:20][S:19][CH:18]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].[CH2:33]([Sn:37](Cl)([CH2:42][CH2:43][CH2:44][CH3:45])[CH2:38][CH2:39][CH2:40][CH3:41])[CH2:34][CH2:35][CH3:36]>C1COCC1>[CH2:42]([Sn:37]([CH2:33][CH2:34][CH2:35][CH3:36])([CH2:38][CH2:39][CH2:40][CH3:41])[C:18]1[S:19][CH:20]=[C:21]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:17]=1[O:16][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH2:43][CH2:44][CH3:45]

Participants

Conditions

Temperature: -40 °C

Procedure

n-Butyllithium (1.8 mL, 4.5 mmol, 2.5 M solution in hexane) was added dropwise at -78° C. to a solution of 3,4-didecyloxythiophene (1.86 g, 4.69 mmol) in anhydrous THF (200 mL) under nitrogen. The solution was stirred for 1 h and warmed to -40° C. Tributylstannyl chloride (1.47 g, 4.52 mmol) was added and the entire solution was finally allowed to warm to room temperature. At room temperature the mixture was filtered using Celite and the solvent was stripped. The organo-tin compound was vacuum dried to give 2-(tributylstannyl)-3,4-didecyloxythiophene, obtained as a light yellow liquid, yield=99%. MS(EI) m/z (rel int): 629 [(M)+ --C4H9, 22%], 396 [(M+ --C12H27Sn), 8.5%], 256 [(M+ --C22H47Sn), 3%] and 116 [(M+ --C32H67Sn), 43%].

Workup

temperatureto warm to room temperature
filtrationAt room temperature the mixture was filtered
customdried

Sources & evidence

ORD record: ord-73733c3a78f24f87986409ba0a0d89ec
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06130339

Reaction notes

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