Pivalic acid → HCID 131719272, compound

HRID 2396651Notes

Reaction equation

HRID 2396651 reaction equation
[Si:1]([O:8][C:9]1[C:17]([CH2:18][CH:19](O)[C:20]([CH3:33])=[CH:21][CH2:22]C(C)C(C)(O[SiH3])C(C)(C)C)=[C:16]([O:35][CH3:36])[C:15]([CH3:37])=[C:14]2[C:10]=1[C:11](=[O:38])[O:12][CH2:13]2)(C(C)(C)C)([CH3:3])[CH3:2].C(O)(=O)[C:40]([CH3:43])([CH3:42])[CH3:41]>C(OCC)(OCC)(OCC)C.CCOCC>[Si:1]([O:8][C:9]1[C:17]([CH2:18]/[CH:19]=[C:20](\[CH3:33])/[CH:21]([CH2:22][CH2:17][CH2:9][O:8][Si:1]([C:40]([CH3:41])([CH3:42])[CH3:43])([CH3:3])[CH3:2])[CH2:10][C:11]([O:12][CH2:13][CH3:14])=[O:38])=[C:16]([O:35][CH3:36])[C:15]([CH3:37])=[C:14]2[C:10]=1[C:11](=[O:38])[O:12][CH2:13]2)([C:20]([CH3:21])([CH3:33])[CH3:19])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 6417Pivalic acidHCID 131719273HCID 131719273, compound

Product 1

HCID 131719272HCID 131719272, compoundYield 276.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 66221Triethyl orthoacetateSolvent

Procedure

7-(4-tert-butyldimethylsilyloxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-1-tert-butyldimethyl-silyloxy-6-hydroxy-5-methylhept-4-ene (4.74 g) was dissolved in triethyl orthoacetate (76 ml) and pivalic acid (171mg) was added. The solution was placed in an oil bath preheated to 130° C., and stirred for 21/2 hrs. ter cooling, the reaction was diluted with ether, washed with 1N NaHSO4 (3X), saturated sodium bicarbonate, brine, and dried. The solvent was evaporated and the resulting oil chromatographed on silica gel (20% ethyl acetate in hexanes) to give ethyl (E) 6-(4-tert-butyldimethylsilyloxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-3-(3-tert-butyldimethylsilyloxypropyl)-4-methylhex-4-enoate (2.94 g), a compound of Formula 802.

Workup

  1. customThe solution was placed in an oil bath
  2. custompreheated to 130° C.
  3. temperatureter cooling
  4. washwashed with 1N NaHSO4 (3X), saturated sodium bicarbonate, brine
  5. customdried
  6. customThe solvent was evaporated
  7. customthe resulting oil chromatographed on silica gel (20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-e009f855bde9477aa596806087160e93
Source dataset
uspto-grants-1996_02
Patent number
US05493030

Reaction notes

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