2-Bromopropene → HCID 19888969, compound

HRID 654330Notes

Reaction equation

HRID 654330 reaction equation
Br[C:2]([CH3:4])=[CH2:3].C([Li])(C)(C)C.[CH2:10]([S:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH:16]=[O:17])[C:11]#[CH:12]>C1COCC1.CCCCC>[CH3:4][C:2](=[CH2:3])[CH:16]([C:15]1[CH:18]=[CH:19][CH:20]=[CH:21][C:14]=1[S:13][CH2:10][C:11]#[CH:12])[OH:17]

Participants

6

Reactant 3

HCID 112022-BromopropeneHCID 19888973HCID 19888973, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 19888969HCID 19888969, compound

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To 2-bromopropene (4.53 g, 37.4 mmol) in 85 ml of dry THF at -78° C. was added t-butyllithium (44 ml of a 1.7M solution in pentane) dropwise. After 2 hours, 2-(2-propynylthio) benzaldehyde (3.0 g, 17.0 mmol) prepared according to the procedures described in Example 1, Steps A, B, and C in 30 ml of dry THF was added dropwise. The reaction mixture was allowed to warm up to room temperature (RT). The reaction mixture was quenched with 100 ml of a saturated NH4Cl solution, extracted twice with diethyl ether, washed with water and brine, and then dried over K2CO3 to afford the subtitle compound.

Workup

  1. additionwas added dropwise
  2. customThe reaction mixture was quenched with 100 ml of a saturated NH4Cl solution
  3. extractionextracted twice with diethyl ether
  4. washwashed with water and brine
  5. dry with materialdried over K2CO3

Sources & evidence

ORD record
ord-995da99e54a74c18aa7cd7070ffda89f
Source dataset
uspto-grants-1992_07
Patent number
US05130485

Reaction notes

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