Water → HCID 20071447, 화합물

HRID 568879

반응식

HRID 568879 반응식
C([Li])CCC.[Br-].[OH:7][CH2:8][CH2:9][CH2:10][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH3:30][O:31][C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][C:39]=1[O:40][CH2:41][O:42][CH3:43])[CH:35]=O.O>C1COCC1>[CH3:30][O:31][C:32]1[CH:33]=[C:34](/[CH:35]=[CH:10]/[CH2:9][CH2:8][OH:7])[CH:37]=[CH:38][C:39]=1[O:40][CH2:41][O:42][CH3:43]

참가 물질

6

반응물 4

HCID 962WaterHCID 796613-Methoxy-4-(methoxymethoxy)benzaldehydeHCID 11025793Phosphonium, (3-hydroxypropyl)triphenyl-, bromideHCID 178418339Butyllithium

생성물 1

HCID 20071447HCID 20071447, 화합물수율 35.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

n-Butyllithium (1.6M in hexane, 25 ml) was added dropwise to a stirred suspension of (3-hydroxypropyl)triphenylphosphonium bromide (8.03 g) in dry THF (50 ml) cooled to 0° under nitrogen. The resulting blood-red solution was stirred at 0° for 10 min and then 3-methoxy-4-(methoxymethoxy)-benzaldehyde (3.60 g) in dry THF (10 ml) was added dropwise over 5 min. The mixture was allowed to warm to room temperature, stirred for 4 h, water (10 ml) was added and the majority of the solvent was removed in vacuo at 40°. A solution of the residual oil in ER (200 ml) was washed with water (150 ml), dried, treated with charcoal, concentrated and purified by FCC eluting with EA-H (1:1) to give the title compound (1.55 g). T.l.c. (EA-H 1:1) Rf 0.30.

후처리

  1. temperaturecooled to 0° under nitrogen
  2. stirringstirred for 4 h
  3. customthe majority of the solvent was removed in vacuo at 40°
  4. washA solution of the residual oil in ER (200 ml) was washed with water (150 ml)
  5. customdried
  6. additiontreated with charcoal
  7. concentrationconcentrated
  8. custompurified by FCC
  9. washeluting with EA-H (1:1)

출처 및 근거

ORD 기록
ord-6969517f20b34f40ad438433119293c4
출처 데이터셋
uspto-grants-1988_03
특허 번호
US04730008

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