Pivaloyl chloride → HCID 22855818, compound

HRID 1757695Notes

Reaction equation

HRID 1757695 reaction equation
[C:1](Cl)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[CH3:8][C@H:9]([CH2:12][C@H:13]([OH:38])[C@@H:14]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C@@H:15]([O:28][CH3:29])[CH2:16][C@@H:17]([CH3:27])[CH2:18][O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH2:10][OH:11]>N1C=CC=CC=1>[C:1]([O:11][CH2:10][C@H:9]([CH3:8])[CH2:12][C@H:13]([OH:38])[C@@H:14]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C@@H:15]([O:28][CH3:29])[CH2:16][C@@H:17]([CH3:27])[CH2:18][O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 10917442HCID 10917442, compound

Product 1

HCID 22855818HCID 22855818, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
25 °C

Procedure

Pivaloyl chloride (870 microliters, 1.05 equiv) was added to a solution of (2R,4S,5R,6S,8R)-2,8-dimethyl-4-hydroxy-5-benzyloxy-6-methoxy-9-t-butyldimethylsilyloxynonanol 21 (Source: Askin, D.; Volante, R. P.; Reamer, R. A.; Ryan, K. M.; Shinkai, I.; Tetra. Lett., 1988, 29, 277.) (3.07 g, 6.75 mmol) in 50 ml of anhydrous pyridine at 0° C. The solution was warmed to 25° C. over 1 hr and then was stirred at 25° C. for 16 hr. The reaction mixture was quenched by the addition of 10 ml of saturated aqueous sodium bicarbonate solution and then partitioned between75 ml of water and 150 ml of diethyl ether. The aqueous phase was extractedwith an additional 2×100 ml portions of ether. The organic phases were combined, washed with 1×50 ml of water and 1×50 ml of saturated sodium chloride solution, and dried over magnesium sulfate. Concentration in vacuo gave 3.67 g of 22 as a crude oil. The oil was purified by chromatography on 180 g of silica gel eluting with 5:1 hexanes:ethylacetate to give 3.52 g of pivaloate 22 (97% yield). The material was homogeneous by 1H and 13C NMR.

Workup

  1. customat 0° C
  2. customThe reaction mixture was quenched by the addition of 10 ml of saturated aqueous sodium bicarbonate solution
  3. custompartitioned between75 ml of water and 150 ml of diethyl ether
  4. washwashed with 1×50 ml of water and 1×50 ml of saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-4075e7e2aa7740c0bf4b779cd3267f92
Source dataset
uspto-grants-1995_08
Patent number
US05446158

Reaction notes

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