2-Methyl-2-butene → HCID 78383926, compound

HRID 1636767Notes

Reaction equation

HRID 1636767 reaction equation
Cl([O-])=O.[Na+].P([O-])(O)(O)=[O:6].[Na+].C/[C:12](=[CH:17]\[CH2:18][CH2:19]/[C:20](/C)=[CH:21]/[CH2:22][O:23]C1CCCCO1)/[CH2:13][CH2:14][CH:15]=O.CC(=CC)C>O.C(O)(C)(C)C>[C:22]([OH:23])(=[O:6])[CH2:21][CH2:20][CH:19]=[CH:18][CH2:17][CH2:12][CH:13]=[CH:14][CH3:15]

Participants

7

Reactant 4

HCID 105532-Methyl-2-buteneHCID 14039070HCID 14039070, compoundHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

Product 1

HCID 78383926HCID 78383926, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

A.a) A solution of 105 g of 80% sodium chlorite and 100 g of sodium dihydrogen phosphate in 1 l of water is added within 30 min. to 50 g of (4E,8E)-(RS)-4,8-dimethyl-10-(tetrahydro-pyran-2-yloxy)-deca-4,8-dienal in 1.5 l of tert-butanol and 1.5 1 of 2-methyl-2-butene. After 2 1/2 hrs. at room temperature the mixture is concentrated and the residue is taken up in methylene chloride, washed with ice-water and 10% potassium hydrogen sulphate solution and dried. 46.5 g of (4E,8E)-(RS)-4,8-dimethyl-10-(tetrahydro-pyran-2-yloxy])-deca-4,8-dienoic acid are obtained. The acid obtained is dissolved in 590 ml of methylene chloride and treated at 0° C. with 14.9 ml of N-allyl-methyl-amine, 32.0 g of N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride and 1.88 g of dimethylaminopyridine. After 3 hrs. at room temperature and working up with methylene chloride/10% potassium hydrogen sulphate and subsequently saturated sodium hydrogen carbonate solution the organic phase is dried and concentrated. 52.3 g of crude (4E,8E)-(RS)-4,8-dimethyl-1 0-(tetrahydro-pyran-2-yloxy)-deca-4,8-dienoic acid allyl-methylamide are obtained.

Workup

  1. customAfter 2 1/2 hrs
  2. concentrationat room temperature the mixture is concentrated
  3. washwashed with ice-water and 10% potassium hydrogen sulphate solution
  4. customdried

Sources & evidence

ORD record
ord-aae7e5f9d94b4727b9efbfe4a1a62743
Source dataset
uspto-grants-2000_03
Patent number
US06034275

Reaction notes

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