Hydrochloric Acid → HCID 72385632, compound

HRID 1364004Notes

Reaction equation

HRID 1364004 reaction equation
[O:1]1[C:5]2([CH2:16][CH2:15][CH2:14][C:7]3([CH2:11][CH2:10][CH:9]([CH2:12][OH:13])[CH2:8]3)[CH2:6]2)[O:4][CH2:3][CH2:2]1.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.Cl>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[O:1]1[C:5]2([CH2:16][CH2:15][CH2:14][C:7]3([CH2:11][CH2:10][CH:9]([CH2:12][O:13][S:23]([C:20]4[CH:21]=[CH:22][C:17]([CH3:27])=[CH:18][CH:19]=4)(=[O:25])=[O:24])[CH2:8]3)[CH2:6]2)[O:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 66936723HCID 66936723, compound

Product 1

HCID 72385632HCID 72385632, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a solution of (1,4-dioxa-dispiro[4.1.4.3]tetradec-9-yl)methanol (14a) (1.20 g, 5.3 mmol) in dry pyridine (12 mL) at 0° C. was added 4-dimethylamino-pyridine (catalytic amount) and p-toluenesulfonyl chloride (2.04 g, 10.6 mmol). The reaction mixture was stirred at room temperature for 24 hours and then poured into a 2 M HCl solution (50 mL). The aqueous solution was extracted with CH2Cl2 and the combined organic layers were washed with a 2 M HCl solution and then with a saturated K2CO3 solution. After drying over anhydrous MgSO4, the solvent was removed in vacuo to afford the desired product as a colorless oil which was used without further purification in the next step.

Workup

  1. extractionThe aqueous solution was extracted with CH2Cl2
  2. washthe combined organic layers were washed with a 2 M HCl solution
  3. dry with materialAfter drying over anhydrous MgSO4
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-03759156e39b4964afb3cf319b8b3852
Source dataset
uspto-grants-2011_02
Patent number
US07888338B2

Reaction notes

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