Lithium diisopropylamide → HCID 42614041, compound

HRID 587900Notes

Reaction equation

HRID 587900 reaction equation
Br[CH:2]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][CH:6]([OH:14])[C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=2[CH:3]1Br.C([N-]C(C)C)(C)C.[Li+]>O1CCCC1>[CH:18]1[C:4]2[C:3]#[C:2][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[CH2:7][CH:6]([OH:14])[C:5]=2[CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 2724682Lithium diisopropylamideHCID 56590415HCID 56590415, compound

Product 1

HCID 42614041HCID 42614041, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 44 (1.528 g, 4 mmol) in tetrahydrofuran (40 ml) was added dropwise lithium diisopropylamide in tetrahydrofuran (2.0 M) (8 ml, 16 mmol) under an atmosphere of Argon at room temperature. The reaction mixture was stirred for 0.5 hour at room temperature, after which it was quenched by addition of dropwise water (0.5 ml). The solvents were evaporated under reduced pressure, and the residue was purified by flash chromatography on silica gel (2:1-0:1 v/v hexanes/CH2Cl2) to give the product as white solid (0.503 g, 57%). 1H NMR (300 MHz, CDCl3): δ 7.67 (1H, aromatics), 7.37-7.18 (7H, aromatics), 4.5 (1H, dd, J=2.1, 14.7 Hz, CHOH), 3.0 (1H, dd, J=2.1, 14.7 Hz, CH), 2.8 (1H, dd, J=2.1, 14.7 Hz, CH2). 13C NMR (75 MHz, CDCl3): δ 154.5, 150.6, 128.6, 127.1, 1127.0, 126.0, 125.8, 125.1, 124.7, 123.0, 122.7, 121.7, 111.9, 109.6, 74.2, 47.7.

Workup

  1. customafter which it was quenched by addition of dropwise water (0.5 ml)
  2. customThe solvents were evaporated under reduced pressure
  3. customthe residue was purified by flash chromatography on silica gel (2:1-0:1 v/v hexanes/CH2Cl2)

Sources & evidence

ORD record
ord-4384989e76ac470fa9875e6ad5e1b171
Source dataset
uspto-grants-2016_01
Patent number
US09227943B2

Reaction notes

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