p-Toluenesulfonic acid → HCID 86735829, compound

HRID 866367Notes

Reaction equation

HRID 866367 reaction equation
[S:1]1[CH2:5][CH2:4][S:3][CH:2]1[CH2:6][CH2:7][CH:8]1[CH:19](/[CH:20]=[CH:21]/[CH:22]([OH:28])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:18][CH2:17][C:9]21[O:14][CH2:13][C:12]([CH3:16])([CH3:15])[CH2:11][O:10]2.C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:40]1[CH:45]=[CH:44][CH2:43][CH2:42][CH2:41]1.C([O-])([O-])=O.[Na+].[Na+]>CCOCC>[S:1]1[CH2:5][CH2:4][S:3][CH:2]1[CH2:6][CH2:7][CH:8]1[CH:19](/[CH:20]=[CH:21]/[CH:22]([OH:28])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:18][CH2:17][C:9]21[O:14][CH2:13][C:12]([CH3:16])([CH3:15])[CH2:11][O:10]2.[O:40]1[CH2:41][CH2:42][CH2:43][CH2:44][CH:45]1[O:14][CH:9]1[CH2:17][CH2:18][CH2:19][CH2:20][O:10]1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyran2×HCID 10340Sodium CarbonateHCID 203869041-[7-[(1,3-Dithia-2-cyclopentyl)-ethyl]-3,3-dimethyl-1,5-dioxaspiro[5,4]-dec-8-yl]-trans-1-octene-3-ol

Product 1

HCID 86735829HCID 86735829, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

1.1 g (2.5 mmoles of 1-[7-[(1,3-dithia-2-cyclopentyl)-ethyl]-3,3-dimethyl-1,5-dioxaspiro[5,4]-dec-8-yl]-trans-1-octene-3-ol were dissolved in 20 ml of absolute ether, 20 mg of p-toluenesulfonic acid were added, 1.2 ml (13 mmoles) of dihydropyrane in 10 ml of absolute ether were added dropwise and the whole was stirred for 4 hours at room temperature. 0.2 ml of dihydropyrane was again added. The reaction mixture was allowed to stand overnight and was then stirred for 30 minutes with 0.5 g of solid Na2CO3. The suspension was filtered, the filtrate was concentrated under reduced pressure and the oil that had formed was eluted with cyclohexane-ethyl acetate (9:1) over a silica gel column.

Workup

  1. waitto stand overnight
  2. filtrationThe suspension was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customthe oil that had formed
  5. washwas eluted with cyclohexane-ethyl acetate (9:1) over a silica gel column

Sources & evidence

ORD record
ord-b5ed18aee1354a4a91a8ea2251114516
Source dataset
uspto-grants-1978_07
Patent number
US04098815

Reaction notes

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