Water → HCID 86610101, compound

HRID 1990703Notes

Reaction equation

HRID 1990703 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]1([C:16]#[C:17][CH2:18][CH2:19][CH2:20][OH:21])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1.C(N(CC)CC)C.O>ClCCl>[CH3:1][S:2]([O:21][CH2:20][CH2:19][CH2:18][C:17]#[C:16][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 199555575-(1-Naphthyl)-4-pentyn-1-ol

Product 1

HCID 86610101HCID 86610101, compoundYield 102%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution of 0.85 g (7.42 mmol) of methanesulphonyl chloride in 5 ml of dichloromethane is added dropwise to a solution, cooled with an ice bath, of 1.2 g (5.71 mmol) of 5-(naphth-1-yl)pent-4-yn-1-ol, obtained in stage 3.1., and of 1.6 ml (11.4 mmol) of triethylamine in 12 ml of dichloromethane. The mixture is stirred at 0° C. for 1 hour and then at ambient temperature for 2 hours. 25 ml of water and 75 ml of dichloromethane are subsequently added. The organic phase is separated by settling and is washed with 25 ml of water and then with 25 ml of a saturated aqueous sodium chloride solution. It is dried over magnesium sulphate and evaporated to dryness to produce 1.68 g of product in the form of an orange oil used directly in the following stage.

Workup

  1. customobtained in stage 3.1
  2. waitat ambient temperature for 2 hours
  3. customThe organic phase is separated
  4. washis washed with 25 ml of water
  5. dry with materialIt is dried over magnesium sulphate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-bcf75c7e0af846288cfdcae3b173fb13
Source dataset
uspto-grants-2010_01
Patent number
US07645757B2

Reaction notes

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