HCID 14039070, compound → HCID 22966931, compound

HRID 2306505Notes

Reaction equation

HRID 2306505 reaction equation
Cl([O-])=O.[Na+].P([O-])(O)(O)=[O:6].[Na+].[CH3:11]/[C:12](=[CH:17]\[CH2:18][CH2:19]/[C:20](/[CH3:30])=[CH:21]/[CH2:22][O:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][O:25]1)/[CH2:13][CH2:14][CH:15]=[O:16]>O.C(O)(C)(C)C.CC(=CC)C>[CH3:11]/[C:12](=[CH:17]\[CH2:18][CH2:19]/[C:20](/[CH3:30])=[CH:21]/[CH2:22][O:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][O:25]1)/[CH2:13][CH2:14][C:15]([OH:6])=[O:16]

Participants

7

Reactant 3

HCID 14039070HCID 14039070, compoundHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

Product 1

HCID 22966931HCID 22966931, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 105532-Methyl-2-buteneSolvent

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 l of 2-methyl-2-butene. After 2½ 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-yloxyl)-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-10-(tetrahydro-pyran-2-yloxy)-deca-4,8-dienoic acid allyl-methylamide are obtained.

Workup

  1. waitAfter 2½ 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-ceb6b0111d9f4a08bb8bb42837ed86db
Source dataset
uspto-grants-2002_08
Patent number
US06441177B1

Reaction notes

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