Pivalic acid → HCID 131719272, compound

HRID 1781565Notes

Reaction equation

HRID 1781565 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 131720027HCID 131720027, compound

Product 1

HCID 131719272HCID 131719272, compoundYield 276.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 66221Triethyl orthoacetateSolvent

Procedure

(E)-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 (171 mg) was added. The solution was placed in an oil bath preheated to 130° C., and stirred for 2 1/2 hrs. After cooling, the reaction was diluted with ether, washed with 1N NaHSO4 (3×), 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. temperatureAfter cooling
  4. washwashed with 1N NaHSO4 (3×), 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-b4a749ba1a50456f8151b855f22ae779
Source dataset
uspto-grants-1997_05
Patent number
US05633279

Reaction notes

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